WO1994027561A1 - Compositions comprising amino acid derivatives, their methods of preparation and use - Google Patents

Compositions comprising amino acid derivatives, their methods of preparation and use Download PDF

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Publication number
WO1994027561A1
WO1994027561A1 PCT/FR1994/000610 FR9400610W WO9427561A1 WO 1994027561 A1 WO1994027561 A1 WO 1994027561A1 FR 9400610 W FR9400610 W FR 9400610W WO 9427561 A1 WO9427561 A1 WO 9427561A1
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WIPO (PCT)
Prior art keywords
formula
composition according
amino acids
compound
protein
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PCT/FR1994/000610
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French (fr)
Inventor
Paul Gacon
Christian Berger
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Givaudan-Lavirotte
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Publication of WO1994027561A1 publication Critical patent/WO1994027561A1/en

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/37—Mixtures of compounds all of which are anionic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/645—Proteins of vegetable origin; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/49—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof

Definitions

  • compositions comprising amino acid derivatives, processes for their preparation and their uses
  • the present invention relates to compositions comprising amino acid derivatives based on amino acids or oligopeptides, having improved organoleptic characteristics, processes for preparing such compositions and their uses, in particular in the fields of cosmetics, hygiene or as a surfactant.
  • N-acylated amino acid derivatives and compositions comprising a mixture of amino acid derivatives and / or N-acylated oligopeptides are well known.
  • Such derivatives and compositions, as well as their uses in various technical fields have been described, for example, in European patent application 308,278 and in international patent applications 92.20647 and 92.21318.
  • acylation reaction can be carried out at a temperature of the order of 30 to 60 ° C., the pH of the hydrolyzate being adjusted to a value greater than 7.
  • This acylation reaction can be carried out, if necessary, in the presence of an organic solvent such as a low molecular weight alcohol such as isopropanol.
  • the temperature of the reaction medium formed is raised to more than 75 ° C., and its pH is brought to a value less than 3, generally less than 2, by means of a strong acid, like hydrochloric acid.
  • the organic phase containing the N-acylated derivatives is separated. of said reaction medium. This separation can for example be carried out by decantation or filtration.
  • the N-acylated derivatives in acid form thus obtained usually have the appearance of a wax. If on the contrary, it is desired to obtain N-acylated derivatives in salified form, the organic phase obtained is neutralized as indicated above, with an organic or inorganic base, chosen in an appropriate manner.
  • the product obtained after separation from the reaction medium is in solid form or in a solution.
  • N-acylated derivatives in salified form therefore requires an acidification step at a pH below 3 followed by a step of separation from the reaction medium. These two steps are mandatory for the preparation of a clear product.
  • the N-acylated derivatives can have very variable organoleptic characteristics, in particular color and odor.
  • composition of N-acylated derivatives prepared from a wheat protein hydrolyzate exhibited less significant coloring than a composition obtained from a soy protein hydrolyzate.
  • compositions derived from wheat proteins as indicated above may no longer meet the desired organoleptic characteristics.
  • N-acylated derivatives in solid form in particular those whose carboxylic functions are free, have a high melting point, which can make their formulations with certain compounds, such as fatty substances, difficult. There has therefore been a need for N-acylated derivatives having a lower melting point.
  • the present invention therefore relates to compositions comprising derivatives of amino acids and / or N-acylated oligopeptides having organoleptic characteristics, in particular an odor and a color, meeting the increasingly high requirements of users, particularly in the fields of cosmetics and hygiene products.
  • compositions have a melting point such that they can be easily formulated with compounds such as fatty substances.
  • the invention thus relates to a composition comprising derivatives of amino acids, characterized in that it comprises:
  • R is a linear or branched, saturated or unsaturated C 1 - C 30 aliphatic radical
  • R 2 is a C 1 - C 5 aliphatic radical, saturated or unsaturated, linear or branched,
  • R 3 is the remainder of an amino acid identical or different from R 1 ,
  • - n is an integer between 0 and 8.
  • a composition according to the invention exhibits organoleptic characteristics, in particular a clearly attenuated odor and color, as well as a lower melting point. than a similar composition, not comprising a compound of formula (II).
  • m represents the average value of the degree of condensation of the amino acids. So when m is equal to 1, the compounds of formula (I) are derived from amino acids. When m is strictly greater than 1, the compounds of formula (I) are derived from oligopeptides consisting of identical or different amino acid condensates, or, when the composition according to the invention comprises more than one compound of formula (I ), a mixture of such oligopeptides and individualized amino acids.
  • each of these units comprising an amino acid residue R 1 identical or different from that of the other units.
  • m is preferably between 1 and 1.8.
  • R 1 and R 3 can constitute amino acid residues constituting a protein.
  • These amino acids can more particularly consist of alanine, arginine, aspartic acid, cysteine, cystine, phenylalanine, glutamic acid, glycine, histidine, leucine, isoleucine, lysine, methionine, serine, threonine, tryptophan, valine, hydroxylysine, tyrosine, asparagine, glutamine, omithine, proline or hydroxyproline.
  • compositions of the invention may comprise a mixture of compounds of formula (I) derived from a hydrolyzate of a protein in which each of the amino acids and / or of oligopeptides constituting said hydrolyzate, is N-acylated by an R-CO radical -, R having one of the meanings indicated below.
  • compositions according to the present invention may also comprise a mixture of compounds of formula (I) derived from a total hydrolyzate reconstituted of a protein, each of the amino acids constituting said hydrolyzate being N-acylated by a radical R-CO-, R having the meaning indicated above.
  • total hydrolyzate is meant in the context of the present invention, an association of amino acids which can be obtained by simple mixing of each of the amino acids, the nature of which is identical to that of each of the amino acids constituting a given protein. . Before mixing, each of these amino acids is in individualized form.
  • a total hydrolyzate reconstituted with a wheat protein can be obtained by mixing amino acids, each of these amino acids being previously selected so that its nature is identical to that of each of the constituent amino acids of wheat protein.
  • amino acids forming such a reconstituted total hydrolyzate are generally commercially available. They can be prepared in a conventional manner by chemical or enzymatic synthesis, or by fermentation. They can also be obtained in known manner, by separation from mixtures of amino acids resulting from the hydrolysis of a protein or a peptide.
  • a total reconstituted hydrolyzate according to the invention may contain only the amino acids constituting a protein, the content of which in said protein is greater than 1% by weight or 2% by weight, relative to the total weight of the acids. protein amines.
  • Table I indicates typical amino acid compositions of several proteins of various origins.
  • the silk protein is made up of 17 amino acids.
  • a total hydrolyzate reconstituted according to the invention can comprise each of these 17 amino acids or, if desired, only those whose content in this silk protein is greater than or equal to 1% by weight, ie 11 amino acids or only those whose content is greater than or equal to 2% by weight, ie 7 amino acids only.
  • the content by weight of each of the amino acids constituting the total reconstituted hydrolyzate may be the content by weight of this same amino acid in the protein, this to within 50%, preferably to within 10%.
  • a total reconstituted hydrolyzate corresponding to that of the silk protein will contain the constituent amino acids of the silk protein in a content of plus or minus 50%, or plus or minus 10%, the content of the same amino acid when it is part of the silk Drotein.
  • the glycine content in the total reconstituted hydrolyzate can be between 34.65 - (0.5 ⁇ 34.65) and 34.65 + (0.5 ⁇ 34.65), i.e. between 17.325 g and 51.975 g per 100 g of amino acids, in the total hydrolyzate reconstructed.
  • Such reconstituted total hydrolysates, as well as their preparation process, are described in detail in French patent application 93.05906 filed on
  • the proteins from which said hydrolysates are derived, or the proteins from which said reconstituted total hydrolysates are prepared can be of animal, vegetable or microorganism origin.
  • a composition according to the invention which is particularly advantageous, comprises a compound of formula (II) in which R 2 is a methyl radical or n is equal to 0.
  • Very particularly preferred compounds of formula (II) consist of sarcosine N-acylated with an R-CO- radical or in sarcosine salts N-acylated with an R-CO- radical.
  • a preferred composition according to the invention comprises compounds of formula (I) and (II) for which the R-CO- group represents a radical chosen from the group consisting of the propionyl, capryloyl, octanoyl, undecylenoyl, lauroyl, cocoyl radical, palmitoyl, stearoyl or oleoyl.
  • the cation M can represent hydrogen, an ammonium ion, a cation of a metal, such as an alkali metal such as sodium or potassium, an alkaline earth metal, aluminum, copper, zinc, cobalt, manganese or the cation of an organic base, such as arginine, lysine, morpholine, choline, ornithine, histidine, monoethanolamine, diethanolamine or triethanolamine.
  • a metal such as an alkali metal such as sodium or potassium, an alkaline earth metal, aluminum, copper, zinc, cobalt, manganese or the cation of an organic base, such as arginine, lysine, morpholine, choline, ornithine, histidine, monoethanolamine, diethanolamine or triethanolamine.
  • a composition according to the invention can be either in solid form or in the form of an aqueous solution.
  • M represents hydrogen
  • said composition is in the form of a wax.
  • the molar ratio between the compound of formula (I) and the compound of formula (II) is between 0.2 and 5, preferably between 0.5 and 2.
  • a composition according to the invention can be obtained by reacting simultaneously, and in a conventional manner, at least one precursor of a compound of formula (I) and at least one precursor of a compound of formula (II), with an agent acylation.
  • Such a reaction is usually carried out in aqueous solution, with or without the presence of an organic solvent such as a low molecular weight alcohol, such as isopropanol.
  • a precursor of a compound of formula (I) consists of an amino acid or an oligopeptide.
  • the precursors can then consist of mixtures of amino acids, oligopeptides or amino acids and oligopeptides.
  • Such mixtures can be protein hydrolysates, or total reconstituted protein hydrolysates as defined above.
  • a precursor of a compound of formula (II) can consist of a compound of formula (III). in which R 2 , R 3 and n have the meanings indicated above for the compounds of formula (II) and M 'is a cation having one of the meanings of M.
  • M ′ can be hydrogen or a cation of an alkali metal such as sodium or potassium.
  • the compound of formula (III) is preferably sarcosine or a sarcosine salt such as sodium or potassium sarcosinate.
  • the acylating agent used is usually an activated derivative of a carboxylic acid of formula RCOOH, R being as indicated above.
  • Derivatives of this type may consist of the symmetrical anhydride of RCOOH, or of acid halides, such as chlorides or acid bromides, of formula
  • the acylation reaction between said precursors and the acylating agent is carried out at a pH greater than 7, more generally greater than 8, and at a temperature between 30 and 60 ° C.
  • the pH of the reaction medium resulting from the acylation reaction is adjusted to a value below 3, generally less than 2 by means of a strong acid.
  • This acidification of the reaction medium is carried out at a temperature generally higher than that of the acylation reaction.
  • the composition according to the invention can then be recovered in a conventional manner.
  • Another object of the invention consists in the use of a composition as described above as a cosmetic agent or as an agent for human or animal hygiene. It can also be used as a surfactant.
  • compositions according to the invention can be formulated in creams, milks, foams, aerosols, gels, sticks, oils, emulsions, soaps, aqueous or hydroalcoholic lotions, shampoos, toothpastes, or in detergent formulations for dishes, floors or laundry.
  • compositions according to the invention can be prepared by mixing an aqueous phase and a fatty phase.
  • the latter usually contains the composition according to the invention.
  • a composition according to the invention has a lower melting point than a composition of the prior art, which is similar but does not contain a compound of formula (II)
  • obtaining a homogeneous fatty phase can be carried out at a lower temperature, which has the main advantage of less degrading the bodies constituting said phase.
  • the sodium salt of the N-lauroyl derivatives of a mixture of aspartic acid, glutamic acid and sarcosine is thus obtained in the form of a clear and practically colorless solution at 30% concentration.
  • the potassium salt of the N-cocoylated derivatives of a mixture of aspartic acid, glutamic acid and sarcosine is thus obtained in the form of a clear solution, and practically colorless at 30% concentration.
  • 2320 g of the sodium salt of the N-lauroyl derivative are thus obtained from a mixture of amino acids of a wheat protein hydrolyzate and of sarcosine in the form of a pale yellow clear liquid at 30% concentration.
  • the lower aqueous phase is drawn off, the organic phase maintained at 60 ° C. is washed with 300 cm 3 of a 10% solution of sodium chloride. After decantation, the aqueous phase is eliminated, the organic phase maintained at 60 ° C. is dried for one hour under reduced pressure (50 mm of mercury) in the reactor with stirring, then poured onto a tray.
  • 120 g of the N-palmitoylated derivative of the mixture of amino acids obtained by hydrolysis of the wheat protein and sarcosine are obtained in the form of a beige waxy solid at 60 ° C.
  • a mixture of 340 g of soy protein, 225 cm 3 of water and 450 cm 3 of hydrochloric acid at 30% w / w is brought to reflux for 8 hours. After cooling, 225 cm 3 of water are added to the reaction mass which is adjusted to pH 3.5 with 495 g of sodium hydroxide at 30% w / w. 20 g of bleaching black are then added, the mixture is left in contact for one hour with stirring and then the suspension is filtered.
  • a similar composition, but not containing N-palmitoyl sarcosine has a melting point of 75 ° C.
  • a shampoo is prepared by mixing, in the order indicated, the following compounds (% by weight) Laurylether (2.2 EO) sodium sulfate 18%
  • a fatty phase A is prepared by mixing the following compounds (% by weight):
  • Phase A is melted at 60 ° C.
  • An emulsion is then formed by mixing 20.5 g of phase A for 79.5 g of water heated to 65 ° C. in a speed 1 emulsifier until complete cooling.

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Abstract

Composition including amino acid derivatives comprising: a) at least one compound derived from an amino acid or an oligopeptide of general formula (I): in which R is a straight or branched, saturated or unsaturated C1-C30 aliphatic radical, R1 is an amino acid residue, M is a cation, and m is 1-5; and b) at least one compound of formula (II) in which R has the same meaning as in formula (I), R2 is a saturated or unsaturated, straight or branched C1-C5 aliphatic radical, R3 is an amino acid residue, the same as or different from R1, M has the same meaning as in formula (I), and n is an integer between 0 and 8. The invention also concerns methods of preparation of such a composition and its use.

Description

Compositions comportant des dérivés d'acides aminés, leurs procédés de préparation et leurs utilisations  Compositions comprising amino acid derivatives, processes for their preparation and their uses
La présente invention concerne des compositions comportant des dérivés d'acides aminés à base d'acides aminés ou d'oligopeptides, présentant des caractéristiques organoleptiques améliorées, des procédés de préparation de telles compositions ainsi que leurs utilisations, notamment dans les domaines de la cosmétique, de l'hygiène ou en tant qu'agent tensioactif.  The present invention relates to compositions comprising amino acid derivatives based on amino acids or oligopeptides, having improved organoleptic characteristics, processes for preparing such compositions and their uses, in particular in the fields of cosmetics, hygiene or as a surfactant.
Les dérivés d'acides aminés N-acylés et les compositions comprenant un mélange de dérivés d'acides aminés et/ou d'oligopeptides N-acylés, sont bien connus. De tels dérivés et compositions, ainsi que leurs utilisations dans divers domaines techniques ont été décrits, par exemple, dans la demande de brevet européen 308.278 et dans les demandes de brevet internationales 92.20647 et 92.21318.  N-acylated amino acid derivatives and compositions comprising a mixture of amino acid derivatives and / or N-acylated oligopeptides are well known. Such derivatives and compositions, as well as their uses in various technical fields have been described, for example, in European patent application 308,278 and in international patent applications 92.20647 and 92.21318.
Ils peuvent notamment être préparés à partir d'un acide aminé ou d'un hydrolysat de protéines comprenant une solution aqueuse d'un mélange d'acides aminés, d'oligopeptides ou d'acides aminés et d'oligopeptides, que l'on fait réagir avec un agent d'acylation. La réaction d'acylation est habituellement effectuée à une température de l'ordre de 30 à 60°C, le pH de l'hydrolysat étant ajusté à une valeur supérieure à 7. Cette réaction d'acylation peut être effectuée, le cas échéant, en présence d'un solvant organique tel un alcool de bas poids moléculaire comme l'isopropanol. A la fin de la réaction d'acylation, on élève à plus de 75°C la température du milieu reactionnel formé, et son pH est amené à une valeur inférieure à 3, généralement inférieure à 2, au moyen d'un acide fort, tel l'acide chlorhydrique.  They can in particular be prepared from an amino acid or a protein hydrolyzate comprising an aqueous solution of a mixture of amino acids, of oligopeptides or of amino acids and of oligopeptides, which are made react with an acylating agent. The acylation reaction is usually carried out at a temperature of the order of 30 to 60 ° C., the pH of the hydrolyzate being adjusted to a value greater than 7. This acylation reaction can be carried out, if necessary, in the presence of an organic solvent such as a low molecular weight alcohol such as isopropanol. At the end of the acylation reaction, the temperature of the reaction medium formed is raised to more than 75 ° C., and its pH is brought to a value less than 3, generally less than 2, by means of a strong acid, like hydrochloric acid.
A ce stade, si l'on souhaite obtenir des dérivés N-acylés sous forme acide, c'est-à-dire des produits dans lesquels les fonctions carboxyliques des acides aminés sont libres, on sépare la phase organique contenant les dérivés N-acylés dudit milieu reactionnel. Cette séparation peut par exemple être effectuée par décantation ou filtration. Les dérivés N- acylés sous forme acide ainsi obtenus, présentent habituellement l'aspect d'une cire. Si au contraire, on souhaite obtenir des dérivés N-acylés sous forme salifiée, on neutralise la phase organique obtenue tel qu'indiqué ci-dessus, avec une base organique ou minérale, choisie de manière appropriée. At this stage, if it is desired to obtain N-acylated derivatives in acid form, that is to say products in which the carboxylic functions of the amino acids are free, the organic phase containing the N-acylated derivatives is separated. of said reaction medium. This separation can for example be carried out by decantation or filtration. The N-acylated derivatives in acid form thus obtained, usually have the appearance of a wax. If on the contrary, it is desired to obtain N-acylated derivatives in salified form, the organic phase obtained is neutralized as indicated above, with an organic or inorganic base, chosen in an appropriate manner.
Selon la nature de la base choisie, le produit obtenu après séparation du milieu reactionnel, se présente sous forme solide ou d'une solution.  Depending on the nature of the base chosen, the product obtained after separation from the reaction medium, is in solid form or in a solution.
La préparation des dérivés N-acylés sous forme salifiée requiert donc une étape d'acidification à un pH inférieur à 3 suivi d'une étape de séparation du milieu reactionnel. Ces deux étapes sont obligatoires en vue de la préparation d'un produit limpide.  The preparation of N-acylated derivatives in salified form therefore requires an acidification step at a pH below 3 followed by a step of separation from the reaction medium. These two steps are mandatory for the preparation of a clear product.
Selon la nature de la protéine ou de l'acide aminé utilisé comme produit de départ, les dérivés N-acylés peuvent présenter des caractéristiques organoleptiques, notamment une coloration et une odeur, très variables.  Depending on the nature of the protein or amino acid used as starting material, the N-acylated derivatives can have very variable organoleptic characteristics, in particular color and odor.
A titre d'exemple, il a pu être constaté qu'une composition de dérivés N-acylés préparés à partir d'un hydrolysat de protéines de blé présentait une coloration moins importante qu'une composition issue d'un hydrolysat de protéines de soja.  By way of example, it has been found that a composition of N-acylated derivatives prepared from a wheat protein hydrolyzate exhibited less significant coloring than a composition obtained from a soy protein hydrolyzate.
Or, à présent les fabricants de produits cosmétiques ou de produits destinés à l'hygiène de l'homme ou de l'animal, recherchent des produits présentant une couleur et une odeur qui soient les plus atténuées possible. Dans ces conditions, même des compositions issues de protéines de blé telles qu'indiquées ci-dessus peuvent ne plus répondre aux caractéristiques organoleptiques recherchées.  Now, the manufacturers of cosmetic products or of products intended for human or animal hygiene, are looking for products having a color and an odor which are as attenuated as possible. Under these conditions, even compositions derived from wheat proteins as indicated above may no longer meet the desired organoleptic characteristics.
Par ailleurs, les dérivés N-acylés classiques sous forme solide, notamment ceux dont les fonctions carboxyliques sont libres, présentent un point de fusion élevé, pouvant rendre difficile leurs formulations avec certains composés, tels des corps gras. Un besoin s'est donc fait sentir pour des dérivés N-acylés présentant un point de fusion moins élevé.  Furthermore, the conventional N-acylated derivatives in solid form, in particular those whose carboxylic functions are free, have a high melting point, which can make their formulations with certain compounds, such as fatty substances, difficult. There has therefore been a need for N-acylated derivatives having a lower melting point.
La présente invention concerne donc des compositions comportant des dérivés d'acides aminés et/ou d'oligopeptides N-acylés présentant des caractéristiques organoleptiques, notamment une odeur et une couleur, répondant aux exigences de plus en plus élevées des utilisateurs, notamment dans les domaines de la cosmétique et des produits d'hygiène. The present invention therefore relates to compositions comprising derivatives of amino acids and / or N-acylated oligopeptides having organoleptic characteristics, in particular an odor and a color, meeting the increasingly high requirements of users, particularly in the fields of cosmetics and hygiene products.
Par ailleurs, ces compositions présentent un point de fusion tel qu'elles peuvent être facilement formulées avec des composés tels des corps gras.  Furthermore, these compositions have a melting point such that they can be easily formulated with compounds such as fatty substances.
L'invention concerne ainsi une composition comportant des dérivés d'acides aminés caractérisés en ce qu'elle comprend :  The invention thus relates to a composition comprising derivatives of amino acids, characterized in that it comprises:
a) au moins un composé dérivé d'un acide aminé ou d'un oligopeptide de formule générale (I)
Figure imgf000005_0001
a) at least one compound derived from an amino acid or from an oligopeptide of general formula (I)
Figure imgf000005_0001
dans laquelle : in which :
- R est un radical aliphatique en C 1 - C30 linéaire ou ramifié, saturé ou insaturé, - R is a linear or branched, saturated or unsaturated C 1 - C 30 aliphatic radical,
- R 1 est le reste d'un acide aminé, - R 1 is the remainder of an amino acid,
- M est un cation,  - M is a cation,
- m est compris entre 1 et 5,  - m is between 1 and 5,
et and
b) au moins un composé de formule (II)
Figure imgf000005_0002
b) at least one compound of formula (II)
Figure imgf000005_0002
dans laquelle : in which :
- R a la même signification que dans la formule (I)  - R has the same meaning as in formula (I)
- R2 est un radical aliphatique en C1 - C5, saturé ou insaturé, linéaire ou ramifié, - R 2 is a C 1 - C 5 aliphatic radical, saturated or unsaturated, linear or branched,
- R3 est le reste d'un acide aminé identique ou différent de R 1 ,- R 3 is the remainder of an amino acid identical or different from R 1 ,
- M a la même signification que dans la formule (I), - M has the same meaning as in formula (I),
- n est un entier compris entre 0 et 8.  - n is an integer between 0 and 8.
De manière surprenante, une composition selon l'invention présente des caractéristiques organoleptiques, notamment une odeur et une couleur, nettement atténuées, ainsi qu'un point de fusion moins élevé qu'une composition similaire, ne comportant pas un composé de formule (II). Surprisingly, a composition according to the invention exhibits organoleptic characteristics, in particular a clearly attenuated odor and color, as well as a lower melting point. than a similar composition, not comprising a compound of formula (II).
Dans la formule (I), m représente la valeur moyenne du degré de condensation des acides aminés. Ainsi lorsque m est égal à 1 , les composés de formule (I) sont dérivés d'acides aminés. Lorsque m est strictement supérieur à 1 , les composés de formule (I) sont dérivés d'oligopeptides constitués de condensats d'acides aminés identiques ou différents, ou, lorsque la composition selon l'invention comporte plus d'un composé de formule (I), d'un mélange de tels oligopeptides et d'acides aminés individualisés.  In formula (I), m represents the average value of the degree of condensation of the amino acids. So when m is equal to 1, the compounds of formula (I) are derived from amino acids. When m is strictly greater than 1, the compounds of formula (I) are derived from oligopeptides consisting of identical or different amino acid condensates, or, when the composition according to the invention comprises more than one compound of formula (I ), a mixture of such oligopeptides and individualized amino acids.
Les composés de formule (I) qui sont des dérivés d'oligopeptides comportent des motifs :
Figure imgf000006_0001
The compounds of formula (I) which are derivatives of oligopeptides have units:
Figure imgf000006_0001
chacun de ces motifs comportant un reste d'acide aminé R 1 identique ou différent de celui des autres motifs. each of these units comprising an amino acid residue R 1 identical or different from that of the other units.
Dans le cadre de l'invention, m est de préférence compris entre 1 et 1 ,8.  In the context of the invention, m is preferably between 1 and 1.8.
R 1 et R3 peuvent constituer des restes d'acides aminés constitutifs d'une protéine. Ces acides aminés peuvent plus particulièrement consister en l'alanine, l'arginine, l'acide aspartique, la cystéine, la cystine, la phénylalanine, l'acide glutamique, la glycine, l'histidine, la leucine, l'isoleucine, la lysine, la méthionine, la serine, la thréonine, le tryptophane, la valine, l'hydroxylysine, la tyrosine, l'asparagine, la glutamine, l'omithine, la proline ou l'hydroxyproline. R 1 and R 3 can constitute amino acid residues constituting a protein. These amino acids can more particularly consist of alanine, arginine, aspartic acid, cysteine, cystine, phenylalanine, glutamic acid, glycine, histidine, leucine, isoleucine, lysine, methionine, serine, threonine, tryptophan, valine, hydroxylysine, tyrosine, asparagine, glutamine, omithine, proline or hydroxyproline.
Les compositions de l'invention peuvent comporter un mélange de composés de formule (I) issus d'un hydrolysat d'une protéine dont chacun des acides aminés et/ou des oligopeptides constituant ledit hydrolysat, est N-acylé par un radical R-CO-, R ayant l'une des significations indiquées ci-dessous.  The compositions of the invention may comprise a mixture of compounds of formula (I) derived from a hydrolyzate of a protein in which each of the amino acids and / or of oligopeptides constituting said hydrolyzate, is N-acylated by an R-CO radical -, R having one of the meanings indicated below.
Les procédés de préparation de tels hydrolysats de protéines sont bien connus de l'homme du métier. Les compositions selon la présente invention peuvent également comprendre un mélange de composés de formule (I) issus d'un hydrolysat total reconstitué d'une protéine, chacun des acides aminés constitutifs dudit hydrolysat étant N-acylé par un radical R-CO-, R ayant la signification indiquée plus haut. The processes for preparing such protein hydrolysates are well known to those skilled in the art. The compositions according to the present invention may also comprise a mixture of compounds of formula (I) derived from a total hydrolyzate reconstituted of a protein, each of the amino acids constituting said hydrolyzate being N-acylated by a radical R-CO-, R having the meaning indicated above.
Par hydrolysat total reconstitué, on entend dans le cadre de la présente invention, une association d'acides aminés pouvant être obtenus par simple mélange de chacun des acides aminés dont la nature est identique à celle de chacun des acides aminés constitutifs d'une protéine donnée. Avant leur mélange, chacun de ces acides aminés se présente sous forme individualisée.  By reconstituted total hydrolyzate is meant in the context of the present invention, an association of amino acids which can be obtained by simple mixing of each of the amino acids, the nature of which is identical to that of each of the amino acids constituting a given protein. . Before mixing, each of these amino acids is in individualized form.
A titre d'exemple, un hydrolysat total reconstitué d'une protéine de blé peut être obtenu par mélange d'acides aminés, chacun de ces acides aminés étant préalablement sélectionné de sorte que sa nature soit identique à celle de chacun des acides aminés constitutifs de la protéine de blé.  By way of example, a total hydrolyzate reconstituted with a wheat protein can be obtained by mixing amino acids, each of these amino acids being previously selected so that its nature is identical to that of each of the constituent amino acids of wheat protein.
Les acides aminés formant un tel hydrolysat total reconstitué sont généralement disponibles dans le commerce. Ils peuvent être préparés de manière classique par synthèse chimique ou enzymatique, ou par fermentation. Ils peuvent être également obtenus de manière connue, par séparation à partir de mélanges d'acides aminés résultant de l'hydrolyse d'une protéine ou d'un peptide.  The amino acids forming such a reconstituted total hydrolyzate are generally commercially available. They can be prepared in a conventional manner by chemical or enzymatic synthesis, or by fermentation. They can also be obtained in known manner, by separation from mixtures of amino acids resulting from the hydrolysis of a protein or a peptide.
Un hydrolysat total reconstitué, selon l'invention, peut ne comporter que les acides aminés constitutifs d'une protéine, dont la teneur dans ladite protéine est supérieure à 1 % en poids ou à 2 % en poids, par rapport au poids total des acides aminés de la protéine.  A total reconstituted hydrolyzate according to the invention may contain only the amino acids constituting a protein, the content of which in said protein is greater than 1% by weight or 2% by weight, relative to the total weight of the acids. protein amines.
A titre d'exemple, le tableau I ci-après indique des compositions type en acides aminés de plusieurs protéines d'origines diverses.  As an example, Table I below indicates typical amino acid compositions of several proteins of various origins.
Comme indiqué dans le tableau. I, la protéine de soie est constituée de 17 acides aminés. Un hydrolysat total reconstitué selon l'invention peut comprendre chacun de ces 17 acides aminés ou, si on le souhaite, seulement ceux dont la teneur dans cette protéine de soie est supérieure ou égale à 1 % en poids, soit 11 acides aminés ou seulement ceux dont la teneur est supérieure ou égale à 2 % en poids, soit 7 acides aminés seulement. As shown in the table. I, the silk protein is made up of 17 amino acids. A total hydrolyzate reconstituted according to the invention can comprise each of these 17 amino acids or, if desired, only those whose content in this silk protein is greater than or equal to 1% by weight, ie 11 amino acids or only those whose content is greater than or equal to 2% by weight, ie 7 amino acids only.
La teneur en poids de chacun des acides aminés constituant l'hydrolysat total reconstitué peut être la teneur en poids de ce même acide aminé dans la protéine, cela à plus ou moins 50%, de préférence à plus moins 10 % près.  The content by weight of each of the amino acids constituting the total reconstituted hydrolyzate may be the content by weight of this same amino acid in the protein, this to within 50%, preferably to within 10%.
A titre d'exemple, un hydrolysat total reconstitué correspondant à celui de la protéine de la soie comportera les acides aminés constitutifs de la protéine de la soie en une teneur de plus ou moins 50 % près, ou de plus ou moins 10 % près, de la teneur en le même acide aminé quand il est constitutif de la Drotéine de la soie.  By way of example, a total reconstituted hydrolyzate corresponding to that of the silk protein will contain the constituent amino acids of the silk protein in a content of plus or minus 50%, or plus or minus 10%, the content of the same amino acid when it is part of the silk Drotein.
Ainsi, si l'on prend le cas de la glycine, présente en une teneur de 34,65 g pour 100 g d'acides aminés de la protéine de la soie, la teneur en glycine dans l'hydrolysat total reconstitué peut être comprise entre 34,65 - (0,5 × 34,65) et 34,65 + (0,5 × 34,65), soit entre 17,325g et 51 ,975 g pour 100 g d'acides aminés, dans l'hydrolysat total reconstitué. De tels hydrolysats totaux reconstitués, ainsi que leur procédé de préparation sont décrits en détail dans la demande de brevet français 93.05906 déposée le Thus, if we take the case of glycine, present in a content of 34.65 g per 100 g of amino acids of the silk protein, the glycine content in the total reconstituted hydrolyzate can be between 34.65 - (0.5 × 34.65) and 34.65 + (0.5 × 34.65), i.e. between 17.325 g and 51.975 g per 100 g of amino acids, in the total hydrolyzate reconstructed. Such reconstituted total hydrolysates, as well as their preparation process, are described in detail in French patent application 93.05906 filed on
17 mai 1993 par la demanderesse. May 17, 1993 by the plaintiff.
Les protéines d'où sont issus lesdits hydrolysats, ou les protéines à partir desquelles on prépare lesdits hydrolysats totaux reconstitués peuvent être d'origine animale, végétale ou issues d'un microorganisme.  The proteins from which said hydrolysates are derived, or the proteins from which said reconstituted total hydrolysates are prepared can be of animal, vegetable or microorganism origin.
Une composition selon l'invention particulièrement avantageuse, comporte un composé de formule (II) dans laquelle R2 est un radical méthyle ou n est égal à 0. A composition according to the invention which is particularly advantageous, comprises a compound of formula (II) in which R 2 is a methyl radical or n is equal to 0.
Des composés de formule (II) tout particulièrement préférés consistent en la sarcosine N-acylée par un radical R-CO- ou en les sels de sarcosine N-acylés par un radical R-CO-.  Very particularly preferred compounds of formula (II) consist of sarcosine N-acylated with an R-CO- radical or in sarcosine salts N-acylated with an R-CO- radical.
Une composition préférée selon l'invention comporte des composés de formule (I) et (II) pour lesquels le groupe R-CO- représente un radical choisi dans le groupe constitué par le radical propionyle, capryloyle, octanoyle, undécylénoyle, lauroyle, cocoyle, palmitoyle, stéaroyle ou oléoyle. Le cation M peut représenter l'hydrogène, un ion ammonium, un cation d'un métal, comme un métal alcalin tel le sodium ou le potassium, un métal alcalino-terreux, l'aluminium, le cuivre, le zinc, le cobalt, le manganèse ou le cation d'une base organique, tel l'arginine, la lysine, la morpholine, la choline, l'ornithine, l'histidine, la monoéthanolamine, la diéthanolamime ou la triéthanolamine. A preferred composition according to the invention comprises compounds of formula (I) and (II) for which the R-CO- group represents a radical chosen from the group consisting of the propionyl, capryloyl, octanoyl, undecylenoyl, lauroyl, cocoyl radical, palmitoyl, stearoyl or oleoyl. The cation M can represent hydrogen, an ammonium ion, a cation of a metal, such as an alkali metal such as sodium or potassium, an alkaline earth metal, aluminum, copper, zinc, cobalt, manganese or the cation of an organic base, such as arginine, lysine, morpholine, choline, ornithine, histidine, monoethanolamine, diethanolamine or triethanolamine.
Une composition selon l'invention peut se présenter soit sous forme solide soit sous forme d'une solution aqueuse. Généralement, quand M représente l'hydrogène, ladite composition se présente sous forme d'une cire.  A composition according to the invention can be either in solid form or in the form of an aqueous solution. Generally, when M represents hydrogen, said composition is in the form of a wax.
Habituellement le rapport molaire entre le composé de formule (I) et le composé de formule (II) est compris entre 0,2 et 5, de préférence entre 0,5 et 2.  Usually the molar ratio between the compound of formula (I) and the compound of formula (II) is between 0.2 and 5, preferably between 0.5 and 2.
Une composition selon l'invention peut être obtenue en faisant réagir simultanément, et de manière classique, au moins un précurseur d'un composé de formule (I) et au moins un précurseur d'un composé de formule (II), avec un agent d'acylation. Une telle réaction est habituellement réalisée en solution aqueuse, en présence ou non d'un solvant organique comme un alcool de bas poids moléculaire, tel l'isopropanol.  A composition according to the invention can be obtained by reacting simultaneously, and in a conventional manner, at least one precursor of a compound of formula (I) and at least one precursor of a compound of formula (II), with an agent acylation. Such a reaction is usually carried out in aqueous solution, with or without the presence of an organic solvent such as a low molecular weight alcohol, such as isopropanol.
Un précurseur d'un composé de formule (I) consiste en un acide aminé ou un oligopeptide.  A precursor of a compound of formula (I) consists of an amino acid or an oligopeptide.
Lorsque la composition selon l'invention comporte plus d'un composé de formule (I), les précurseurs peuvent alors consister en des mélanges d'acides aminés, d'oligopeptides ou d'acides aminés et d'oligopeptides.  When the composition according to the invention comprises more than one compound of formula (I), the precursors can then consist of mixtures of amino acids, oligopeptides or amino acids and oligopeptides.
De tels mélanges peuvent être des hydrolysats de protéines, ou des hydrolysats totaux reconstitués de protéines tels que définis plus haut.  Such mixtures can be protein hydrolysates, or total reconstituted protein hydrolysates as defined above.
Un précurseur d'un composé de formule (II) peut consister en un composé de formule (III).
Figure imgf000009_0001
dans laquelle R2, R3 et n ont les significations indiquées ci-dessus pour les composés de formule (II) et M' est un cation ayant l'une des significations de M. A precursor of a compound of formula (II) can consist of a compound of formula (III).
Figure imgf000009_0001
in which R 2 , R 3 and n have the meanings indicated above for the compounds of formula (II) and M 'is a cation having one of the meanings of M.
Plus particulièrement, M' peut être l'hydrogène ou un cation d'un métal alcalin tel le sodium ou le potassium. Le composé de formule (III) est, de préférence, la sarcosine ou un sel de sarcosine comme le sarcosinate de sodium ou de potassium.  More particularly, M ′ can be hydrogen or a cation of an alkali metal such as sodium or potassium. The compound of formula (III) is preferably sarcosine or a sarcosine salt such as sodium or potassium sarcosinate.
L'agent d'acylation mis en oeuvre est habituellement un dérivé activé d'un acide carboxylique de formule RCOOH, R étant tel qu'indiqué plus haut.  The acylating agent used is usually an activated derivative of a carboxylic acid of formula RCOOH, R being as indicated above.
Des dérivés de ce type peuvent consister en l'anhydride symétrique de RCOOH, ou en des halogénures d'acides, comme des chlorures ou des bromures d'acides, de formule  Derivatives of this type may consist of the symmetrical anhydride of RCOOH, or of acid halides, such as chlorides or acid bromides, of formula
R - COX, où X est un halogène  R - COX, where X is a halogen
Généralement, la réaction d'acylation entre lesdits précurseurs et l'agent d'acylation est réalisée à un pH supérieur à 7, plus généralement supérieur à 8, et à une température comprise entre 30 et 60°C.  Generally, the acylation reaction between said precursors and the acylating agent is carried out at a pH greater than 7, more generally greater than 8, and at a temperature between 30 and 60 ° C.
En vue de l'obtention d'une composition dans laquelle le ou les composés de formule (I) et (II) se présentent sous forme acide, le pH du milieu reactionnel résultant de la réaction d'acylation est ajusté à une valeur inférieure à 3, généralement inférieure à 2 au moyen d'un acide fort. With a view to obtaining a composition in which the compound or compounds of formula (I) and (II) are in acid form, the pH of the reaction medium resulting from the acylation reaction is adjusted to a value below 3, generally less than 2 by means of a strong acid.
Cette acidification du milieu reactionnel est effectuée à une température généralement plus élevée que celle de la réaction d'acylation. On peut alors récupérer la composition selon l'invention de manière classique. This acidification of the reaction medium is carried out at a temperature generally higher than that of the acylation reaction. The composition according to the invention can then be recovered in a conventional manner.
En vue de la préparation d'une composition selon l'invention, où le ou les composés de formule (I) et (II) se présentent sous forme salifiée, c'est-à-dire ceux de ces composés où M est différent de l'hydrogène, on peut directement après la réaction d'acylation, ajuster le pH du milieu reactionnel à une valeur voisine de la neutralité; soit à une valeur habituellement comprise entre 6,5 et 8. Cette neutralisation est effectuée au moyen d'une base comportant le cation M. Suite à quoi, on récupère la composition de manière classique.  For the preparation of a composition according to the invention, where the compound or compounds of formula (I) and (II) are in salified form, that is to say those of these compounds where M is different from hydrogen, it is possible directly after the acylation reaction, to adjust the pH of the reaction medium to a value close to neutrality; either at a value usually between 6.5 and 8. This neutralization is carried out by means of a base comprising the cation M. Following which, the composition is recovered in a conventional manner.
Le procédé de préparation, selon l'invention, d'une telle composition comportant un ou plusieurs composés de formule (I) et de formule (II) sous forme salifiée, ne requiert donc pas comme c'est habituel lors de la préparation de tels sels, une étape d'acidification du milieu reactionnel, suivie d'une étape de séparation du milieu reactionnel de la phase organique comportant lesdits dérivés sous forme libre, ce préalablement à ladite neutralisation. Il est rappelé que ces deux étapes sont habituellement mises en oeuvre en vue de l'obtention d'une composition limpide. Or, et ceci d'une manière tout à fait surprenante, une composition selon l'invention peut être obtenue limpide même en l'absence de ces étapes d'acidification et de séparation. The process for the preparation, according to the invention, of such a composition comprising one or more compounds of formula (I) and of formula (II) in salified form, therefore does not require as is usual during the preparation of such salts, a step of acidification of the reaction medium, followed by a step of separation of the reaction medium from the organic phase comprising said derivatives in free form, this prior to said neutralization. It is recalled that these two stages are usually carried out with a view to obtaining a clear composition. Now, and this quite surprisingly, a composition according to the invention can be obtained clear even in the absence of these acidification and separation steps.
Un tel procédé de préparation obviant aux étapes d'acidification et de séparation est avantageux dans la mesure où il est plus économique, plus simple de mise en oeuvre et moins dégradant pour les composés présents au sein du milieu reactionnel.  Such a preparation process which obviates the acidification and separation stages is advantageous insofar as it is more economical, simpler to use and less degrading for the compounds present in the reaction medium.
Un autre objet de l'invention consiste en l'utilisation d'une composition telle que décrite ci-dessus comme agent cosmétique ou comme agent pour l'hygiène de l'homme ou de l'animal. Elle peut également être utilisée en tant qu'agent tensio-actif.  Another object of the invention consists in the use of a composition as described above as a cosmetic agent or as an agent for human or animal hygiene. It can also be used as a surfactant.
Dans ce type d'utilisation, les compositions selon l'invention peuvent être formulées dans des crèmes, laits, mousses, aérosols, gels, sticks, huiles, émulsions, savons, lotions aqueuses ou hydroalcooliques, shampooings, dentifrices, ou dans des formulations détergentes pour la vaisselle, les sols ou le linge.  In this type of use, the compositions according to the invention can be formulated in creams, milks, foams, aerosols, gels, sticks, oils, emulsions, soaps, aqueous or hydroalcoholic lotions, shampoos, toothpastes, or in detergent formulations for dishes, floors or laundry.
Certaines de ces formulations peuvent être préparées par mélange d'une phase aqueuse et d'une phase grasse. Cette dernière contient habituellement la composition selon l'invention. Dans la mesure où une composition selon l'invention présente un point de fusion plus bas qu'une composition de l'art antérieur, similaire, mais ne comportant pas de composé de formule (II), l'obtention d'une phase grasse homogène peut être réalisée à une température plus basse, ce qui a pour principal avantage de moins dégrader les corps constituant ladite phase.  Some of these formulations can be prepared by mixing an aqueous phase and a fatty phase. The latter usually contains the composition according to the invention. Insofar as a composition according to the invention has a lower melting point than a composition of the prior art, which is similar but does not contain a compound of formula (II), obtaining a homogeneous fatty phase can be carried out at a lower temperature, which has the main advantage of less degrading the bodies constituting said phase.
Les exemples suivants ont pour but d'illustrer la présente invention. Exemple 1 The following examples are intended to illustrate the present invention. Example 1
Préparation d'un sel de sodium des dérivés N-lauroylés d'un mélange d'acide aspartique d'acide glutamique et de sarcosine.  Preparation of a sodium salt of the N-lauroyl derivatives of a mixture of aspartic acid glutamic acid and sarcosine.
A une solution constituée de 20 g d'acide glutamique, 15g d'acide aspartique et de 23,5 g de sarcosine dans 320 cm3 d'eau et portée à pH 10,5 par 90 g de soude à 30 % poids/poids, on ajoute simultanément, sous agitation et de manière à maintenir le pH entre 10 et 11 , 104g de chlorure de lauroyle et 113 g de soude à 30 % poids/poids entre 40 et 60°C. Le milieu reactionnel est ensuite maintenu une heure à 60°C, puis ajusté à pH 7 par 38 g d'acide chlorhydrique à 30 % p/p et dilué par 50 cm3 d'eau. To a solution consisting of 20 g of glutamic acid, 15 g of aspartic acid and 23.5 g of sarcosine in 320 cm 3 of water and brought to pH 10.5 with 90 g of sodium hydroxide at 30% w / w , 104 g of lauroyl chloride and 113 g of sodium hydroxide at 30% w / w between 40 and 60 ° C are added simultaneously, with stirring and in order to maintain the pH between 10 and 11. The reaction medium is then kept for one hour at 60 ° C., then adjusted to pH 7 with 38 g of hydrochloric acid at 30% w / w and diluted with 50 cm 3 of water.
On obtient ainsi le sel de sodium des dérivés N-lauroylés d'un mélange d'acide aspartique, d'acide glutamique et de sarcosine sous forme d'une solution limpide et pratiquement incolore à 30 % de concentration.  The sodium salt of the N-lauroyl derivatives of a mixture of aspartic acid, glutamic acid and sarcosine is thus obtained in the form of a clear and practically colorless solution at 30% concentration.
Exemple 2  Example 2
Préparation d'un sel de potassium des dérivés N-cocoylés d'un mélange d'acide aspartique. d'acide glutamique et de sarcosine.  Preparation of a potassium salt of the N-cocoylated derivatives of a mixture of aspartic acid. glutamic acid and sarcosine.
A une solution constituée de 20 g d'acide glutamique, 15 g d'acide aspartique et de 23,5 g de sarcosine dans 320 cm3 d'eau et portée à pH 10,5 par 76 g de potasse à 50 % poids/poids, on ajoute simultanément, sous agitation, et de manière à maintenir le pH entre 10 et 11 , 1 12g de chlorure de cocoyle et 95 g de potasse à 50 % poids/poids, entre 45 et 55°C. Le milieu reactionnel est ensuite maintenu à 60°C pendant, une heure, puis ajusté à pH 7 par 40 g d'acide chlorhydrique à 30 % poids/poids, et dilué par 150 cm3 d'eau. To a solution consisting of 20 g of glutamic acid, 15 g of aspartic acid and 23.5 g of sarcosine in 320 cm 3 of water and brought to pH 10.5 with 76 g of potash at 50% by weight / by weight, simultaneously with stirring, and so as to maintain the pH between 10 and 11, 1.12 g of cocoyl chloride and 95 g of potassium hydroxide at 50% w / w, between 45 and 55 ° C. are added. The reaction medium is then maintained at 60 ° C for one hour, then adjusted to pH 7 with 40 g of hydrochloric acid at 30% w / w, and diluted with 150 cm 3 of water.
On obtient ainsi le sel de potassium des dérivés N-cocoylés d'un mélange d'acide aspartique, glutamique et de sarcosine sous forme d'une solution limpide, et pratiquement incolore à 30 % de concentration.  The potassium salt of the N-cocoylated derivatives of a mixture of aspartic acid, glutamic acid and sarcosine is thus obtained in the form of a clear solution, and practically colorless at 30% concentration.
Exemple 3  Example 3
Préparation d'un sel de sodium du dérivé N-lauroylé d'un mélange des acides aminés d'un hydrolysat de protéine de blé et de sarcosine  Preparation of a sodium salt of the N-lauroyl derivative of a mixture of amino acids of a hydrolyzate of wheat protein and sarcosine
Un mélange constitué de 375 g de protéine de blé, 225 cm3 d'eau et 450 cm3 d'acide chlorhydrique à 30 % poids/poids est porté pendant 8 heures à reflux. Après refroidissement, 225 cm3 d'eau sont ajoutés à la masse réactionnelle qui est ensuite ajustée à pH 3,5 par 505 g de soude à 30 % poids/poids. On ajoute alors 20 g de noir décolorant, on laisse une heure en contact sous agitation puis on filtre la suspension. A mixture consisting of 375 g of wheat protein, 225 cm 3 of water and 450 cm 3 of hydrochloric acid at 30% w / w is brought for 8 hours at reflux. After cooling, 225 cm 3 of water are added to the reaction mass which is then adjusted to pH 3.5 with 505 g of sodium hydroxide at 30% w / w. 20 g of bleaching black are then added, the mixture is left in contact for one hour with stirring and then the suspension is filtered.
A 800 g de la solution ainsi obtenue, on ajoute 240 g d'une solution à 40 % poids/poids de sarcosinate de sodium puis 105 g de soude à 30 % poids/poids pour ajuster le pH à 10,5, puis on ajoute simultanément, sous agitation, et de manière à maintenir le pH entre 10 et 1 1 , 270,5 g de chlorure de lauroyle et 294 g de soude à 30 % poids/poids entre 35 et 55°C. Le milieu reactionnel est ensuite maintenu une heure à 60°C puis ajusté à pH 7 avec 65 g d'acide chlorhydrique à 30% poids/poids et dilué par 550 cm3 d'eau. To 800 g of the solution thus obtained, 240 g of a 40% w / w solution of sodium sarcosinate are added, then 105 g of sodium hydroxide at 30% w / w to adjust the pH to 10.5, then added simultaneously, with stirring, and so as to maintain the pH between 10 and 11, 270.5 g of lauroyl chloride and 294 g of sodium hydroxide at 30% w / w between 35 and 55 ° C. The reaction medium is then kept for one hour at 60 ° C. and then adjusted to pH 7 with 65 g of hydrochloric acid at 30% w / w and diluted with 550 cm 3 of water.
On obtient ainsi 2320 g du sel de sodium du dérivé N-lauroylé d'un mélange des acides aminés d'un hydrolysat de protéine de blé et de sarcosine sous forme d'un liquide limpide jaune pâle à 30 % de concentration.  2320 g of the sodium salt of the N-lauroyl derivative are thus obtained from a mixture of amino acids of a wheat protein hydrolyzate and of sarcosine in the form of a pale yellow clear liquid at 30% concentration.
Exemple 4  Example 4
Préparation du dérivé N-palmitoylé d'un mélange des acides aminés d'un hydrolysat de la protéine de blé et de sarcosine.  Preparation of the N-palmitoylated derivative of a mixture of amino acids from a hydrolyzate of wheat protein and sarcosine.
A 250 g de l'hydrolysat de protéine de blé obtenu comme à l'exemple 3, on ajoute 75g d'une solution à 40 % poids/poids de sarcosinate de sodium, puis 53 g de soude à 30 % poids/poids, on ajuste le pH à 10,5 et on ajoute 150 cm3 d'isopropanol. On ajoute alors simultanément sous agitation et de manière à maintenir le pH entre 10 et 1 1 , 108 g de chlorure de palmitoyle et 73,5 g de soude à 30 % poids/poids entre 30 et 40°C. Le milieu reactionnel est ensuite maintenu 30 minutes à 60°C sous agitation, puis on ajoute 128 g d'acide chlorhydrique à 30% poids/poids ; on arrête l'agitation pour décanter. La phase aqueuse inférieure est soutirée, la phase organique maintenue à 60°C est lavée par 300 cm3 d'une solution à 10 % de chlorure de sodium. Après décantation, la phase aqueuse est éliminée, la phase organique maintenue à 60°C est séchée pendant une heure sous pression réduite (50 mm de mercure) dans le réacteur sous agitation, puis coulée sur plateau. On obtient 120 g du dérivé N-palmitoylé du mélange des acides aminés obtenu par hydrolyse de la protéine de blé et de sarcosine sous forme d'un solide cireux beige à 60°C. To 250 g of the wheat protein hydrolyzate obtained as in Example 3, 75 g of a 40% w / w sodium sarcosinate solution are added, then 53 g of 30% s / w soda is added. adjust the pH to 10.5 and add 150 cm 3 of isopropanol. 108 g of palmitoyl chloride and 73.5 g of sodium hydroxide at 30% w / w between 30 and 40 ° C. are then added simultaneously with stirring and in order to maintain the pH between 10 and 11. The reaction medium is then maintained for 30 minutes at 60 ° C. with stirring, then 128 g of hydrochloric acid at 30% w / w are added; the agitation is stopped to decant. The lower aqueous phase is drawn off, the organic phase maintained at 60 ° C. is washed with 300 cm 3 of a 10% solution of sodium chloride. After decantation, the aqueous phase is eliminated, the organic phase maintained at 60 ° C. is dried for one hour under reduced pressure (50 mm of mercury) in the reactor with stirring, then poured onto a tray. 120 g of the N-palmitoylated derivative of the mixture of amino acids obtained by hydrolysis of the wheat protein and sarcosine are obtained in the form of a beige waxy solid at 60 ° C.
Exemple 5  Example 5
Préparation du dérivé N-palmitovIé d'un mélange de sarcosine et des acides aminés d'un hydrolysat de protéine de soja  Preparation of the N-palmitov derivative of a mixture of sarcosine and the amino acids of a soy protein hydrolyzate
Un mélange de 340 g de protéine de soja, de 225 cm3 d'eau et de 450 cm3 d'acide chlorhydrique à 30 % poids/poids est porté pendant 8 heures à reflux. Après refroidissement, 225 cm3 d'eau sont ajoutés à la masse réactionnelle qui est ajustée à pH 3,5 par 495 g de soude à 30 % poids/poids. On ajoute ensuite 20 g de noir décolorant, on laisse une heure en contact sous agitation puis on filtre la suspension. A mixture of 340 g of soy protein, 225 cm 3 of water and 450 cm 3 of hydrochloric acid at 30% w / w is brought to reflux for 8 hours. After cooling, 225 cm 3 of water are added to the reaction mass which is adjusted to pH 3.5 with 495 g of sodium hydroxide at 30% w / w. 20 g of bleaching black are then added, the mixture is left in contact for one hour with stirring and then the suspension is filtered.
A 230 g de la solution ainsi obtenue, on ajoute 70 g d'une solution à 40 % poids/poids de sarcosinate de sodium, puis 30 g de soude à 30 % poids/poids pour ajuster le pH à 10,5 et 60 cm3 d'alcool isopropylique. On ajoute alors simultanément sous agitation, et de manière à maintenir le pH entre 10 et 11 , 77 g de chlorure de palmitoyle et 52,4 g de soude à 30 % poids/poids entre 30 et 40°C. Le milieu reactionnel est ensuite maintenu 30 minutes à 60°C sous agitation , puis on ajoute 85 g d'acide chlorhydrique à 30 % poids/poids, on arrête l'agitation et on soutire la phase aqueuse inférieure. La phase organique maintenue à 60°C est lavée par 20 cm3 d'une solution à 10 % de chlorure de sodium. Après décantation, la phase aqueuse est éliminée, la phase organique maintenue à 60°C. et séchée pendant une heure sous pression réduite (50 mm de mercure) dans le réacteur sous agitation, puis coulée sur plateau. To 230 g of the solution thus obtained, 70 g of a 40% w / w solution of sodium sarcosinate are added, then 30 g of sodium hydroxide at 30% w / w to adjust the pH to 10.5 and 60 cm. 3 isopropyl alcohol. Then added simultaneously with stirring, and so as to maintain the pH between 10 and 11, 77 g of palmitoyl chloride and 52.4 g of sodium hydroxide at 30% w / w between 30 and 40 ° C. The reaction medium is then kept for 30 minutes at 60 ° C. with stirring, then 85 g of hydrochloric acid at 30% w / w are added, stirring is stopped and the lower aqueous phase is drawn off. The organic phase maintained at 60 ° C. is washed with 20 cm 3 of a 10% solution of sodium chloride. After decantation, the aqueous phase is eliminated, the organic phase maintained at 60 ° C. and dried for one hour under reduced pressure (50 mm of mercury) in the stirred reactor, then poured onto a tray.
On obtient ainsi 92 g du dérivé N-palmitoylé d'un mélange des acides aminés d'un hydrolysat de protéine de soja et de sarcosine sous forme d'un solide cireux beige fondant vers 60°C.  92 g of the N-palmitoylated derivative of a mixture of amino acids of a soy protein hydrolyzate and of sarcosine are thus obtained in the form of a beige waxy solid melting at around 60 ° C.
Une composition similaire, mais ne comportant pas de N- palmitoyl sarcosine présente un point de fusion de 75°C.  A similar composition, but not containing N-palmitoyl sarcosine has a melting point of 75 ° C.
Exemple 6  Example 6
Shampooing  Shampoo
Un shampooing est préparé en mélangeant, dans l'ordre indiqué les composés suivants (% en poids) Lauryléther (2,2 OE) sulfate de sodium 18 % A shampoo is prepared by mixing, in the order indicated, the following compounds (% by weight) Laurylether (2.2 EO) sodium sulfate 18%
Composition de l'exemple 3 13 % Composition of Example 3 13%
Amonyl 380 BA (1 ) 8 % Amonyl 380 BA (1) 8%
Oramide DL 200 AF (2) 1 ,5 % parfum 0,3 % eau QSP 100 %Oramide DL 200 AF (2) 1.5% perfume 0.3% water QSP 100%
Acide lactique QS pH 7(1) : cocoamidopropyl bétaine commercialisé par la Société SEPPIC FRANCE QS lactic acid pH 7 (1): cocoamidopropyl betaine marketed by SEPPIC FRANCE
(2) : diéthanolamide de coprah commercialisé par la Société SEPPIC FRANCE (2): coconut diethanolamide marketed by SEPPIC FRANCE
Exemple 7  Example 7
Crème hydratante  moisturizer
On prépare une phase grasse A en mélangeant les composés suivants (% en poids) :  A fatty phase A is prepared by mixing the following compounds (% by weight):
Composition de l'exemple 4 10 %  Composition of Example 4 10%
Octyl paramethoxycinnamate 10 %  Octyl paramethoxycinnamate 10%
Benzophénone-3 2,5 %  Benzophenone-3 2.5%
Montanov 68 (1 ) 25 % Montanov 68 (1) 25%
Schercenol DISD™ (2) 25 % Schercenol DISD ™ (2) 25%
Lanol 1688 (3) 25 % Lanol 1688 (3) 25%
huile de silicone 2,5 % 2.5% silicone oil
(1) cétéaryl glucoside commercialisé par la Société SEPPIC (1) cetearyl glucoside sold by the company SEPPIC
(2) Diisostéaryl-dimère-dilinoléate commercialisé par la Société SCHER (3) cétéarylactanoate commercialisé par la Société SEPPIC (2) Diisostearyl-dimer-dilinoleate marketed by the company SCHER (3) cetearylactanoate marketed by the company SEPPIC
La phase A est fondue à 60°C.  Phase A is melted at 60 ° C.
On forme ensuite une émulsion en mélangeant 20,5 g de phase A pour 79,5 g d'eau chauffée à 65°C dans un emulseur vitesse 1 jusqu'à refroidissement complet.  An emulsion is then formed by mixing 20.5 g of phase A for 79.5 g of water heated to 65 ° C. in a speed 1 emulsifier until complete cooling.
A l'émulsion ainsi préparée on ajoute :  To the emulsion thus prepared is added:
- du parfum 0,50 %  - perfume 0.50%
- des conservateurs 0,50 %  - preservatives 0.50%
La préparation d'une même formulation mais comportant uniquement un dérivé N-palmitoylé d'un mélange des acides aminés d'un hydrolysat de protéine de blé, oblige à fondre la phase A à 80°C, et de chauffer l'eau à 85°C pour former l'émulsion. The preparation of the same formulation but comprising only an N-palmitoylated derivative of a mixture of amino acids of a wheat protein hydrolyzate, requires melting phase A at 80 ° C, and heating the water to 85 ° C to form the emulsion.
Figure imgf000017_0001
Figure imgf000017_0001
Figure imgf000018_0001
Figure imgf000018_0001

Claims

REVENDICATIONS
1. Une composition comportant des dérivés d'acides aminés caractérisée en ce qu'elle comprend :  1. A composition comprising amino acid derivatives, characterized in that it comprises:
a) au moins un composé dérivé d'un acide aminé ou d'un oligopeptide de formule générale (I)
Figure imgf000019_0002
1 a) at least one compound derived from an amino acid or from an oligopeptide of general formula (I)
Figure imgf000019_0002
1
dans laquelle : in which :
- R est un radical aliphatique en C1-C30 linéaire ou ramifié, saturé ou insaturé, - R is a linear or branched, saturated or unsaturated aliphatic C 1 -C 30 radical,
- R 1 est le reste d'un acide aminé, - R 1 is the remainder of an amino acid,
- M est un cation,  - M is a cation,
et and
- m est compris entre 1 et 5,  - m is between 1 and 5,
et and
b) au moins un composé de formule (II)
Figure imgf000019_0001
b) at least one compound of formula (II)
Figure imgf000019_0001
dans laquelle : in which :
- R a la même signification que dans la formule (I)  - R has the same meaning as in formula (I)
- R2 est un radical aliphatique, en C1-C5, saturé ou insaturé, linéaire ou ramifié, - R 2 is an aliphatic radical, C 1 -C 5 , saturated or unsaturated, linear or branched,
- R3 est le reste d'un acide aminé identique ou différent de R 1.- R 3 is the remainder of an amino acid identical or different from R 1 .
- M a la même signification que dans la formule (I). - M has the same meaning as in formula (I).
et and
- n est un entier compris entre 0 et 8.  - n is an integer between 0 and 8.
2. Une composition selon la revendication 1 , caractérisée en ce que m est compris entre 1 et 1 ,8.  2. A composition according to claim 1, characterized in that m is between 1 and 1, 8.
3. Une composition selon l'une des revendications 1 et 2, caractérisée en ce qu'elle comprend un mélange de composés de formule (I) issu d'un hydrolysat d'une protéine dont chacun des acides aminés et/ou des oligopeptides constituant ledit hydrolysat est N-acylé par un radical R-CO-, R étant tel que défini dans la revendication 1. 3. A composition according to one of claims 1 and 2, characterized in that it comprises a mixture of compounds of formula (I) derived from a hydrolyzate of a protein each of which amino acids and / or oligopeptides constituting said hydrolyzate is N-acylated by a radical R-CO-, R being as defined in claim 1.
4. Une composition selon l'une des revendications 1 et 2, caractérisée en ce qu'elle comprend un mélange de composés de formule (I) issu d'un hydrolysat total reconstitué d'une protéine, chacun des acides aminés constitutifs dudit hydrolysat étant N-acylé par un radical R-CO, R étant tel que défini dans la revendication 1.  4. A composition according to one of claims 1 and 2, characterized in that it comprises a mixture of compounds of formula (I) derived from a total hydrolyzate reconstituted of a protein, each of the amino acids constituting said hydrolyzate being N-acylated by an R-CO radical, R being as defined in claim 1.
5. Une composition selon la revendication 4, caractérisée en ce que ledit hydrolysat total reconstitué comporte uniquement les acides aminés constitutifs d'une protéine dont la teneur dans ladite protéine est supérieure à 1 % en poids par rapport au poids total des acides aminés de la protéine.  5. A composition according to claim 4, characterized in that said total reconstituted hydrolyzate comprises only the amino acids constituting a protein whose content in said protein is greater than 1% by weight relative to the total weight of amino acids of the protein.
6. Une composition selon la revendication 4, caractérisée en ce que ledit hydrolysat total reconstitué comporte uniquement les acides aminés constitutifs d'une protéine dont la teneur dans ladite protéine est supérieure à 2 % en poids par rapport au poids total des acides aminés de la protéine.  6. A composition according to claim 4, characterized in that said reconstituted total hydrolyzate comprises only the amino acids constituting a protein whose content in said protein is greater than 2% by weight relative to the total weight of amino acids of the protein.
7. Une composition selon l'une des revendications 3 à 6, caractérisée en ce que la protéine est d'origine animale, végétale, ou issue d'un microorganisme.  7. A composition according to one of claims 3 to 6, characterized in that the protein is of animal, vegetable origin, or derived from a microorganism.
8. Une composition selon l'une des revendications précédentes, caractérisée en ce que R2 est un radical méthyle. 8. A composition according to one of the preceding claims, characterized in that R 2 is a methyl radical.
9. Une composition selon l'une des revendications précédentes, caractérisée en ce que n est égal à zéro.  9. A composition according to one of the preceding claims, characterized in that n is equal to zero.
10. Une composition selon l'une des revendications précédentes, caractérisée en ce que le composé de formule (II) est la sarcosine N-acylée par un radical R-CO- ou un sel de sarcosine N-acylé par un radical R-CO -.  10. A composition according to one of the preceding claims, characterized in that the compound of formula (II) is sarcosine N-acylated by an R-CO- radical or a salt of sarcosine N-acylated by an R-CO radical -.
11. Une composition selon l'une des revendications précédentes, caractérisée en ce que M est l'hydrogène.  11. A composition according to one of the preceding claims, characterized in that M is hydrogen.
12. Une composition selon l'une des revendications précédentes, caractérisée en ce que M représente un ion ammonium, un cation d'un métal, comme un métal alcalin tel le sodium ou le potassium, un métal alcalino-terreux, l'aluminium, le cuivre, le zinc, le cobalt, le manganèse ou le cation d'une base organique telle l'arginine, la lysine, la morpholine, la choline, l'ornithine, l'histidine, la monoethanolamine, la diethanolamine ou la triéthanolamine. 12. A composition according to one of the preceding claims, characterized in that M represents an ammonium ion, a cation of a metal, such as an alkali metal such as sodium or potassium, an alkaline earth metal, aluminum, copper, zinc, cobalt, manganese or the cation of an organic base such as arginine, lysine, morpholine, choline, ornithine, histidine, monoethanolamine, diethanolamine or triethanolamine.
13. Une composition selon l'une des revendications précédentes, caractérisée en ce que R-CO- représente un radical choisi dans le groupe constitué par le radical propionyle, capryloyle, octanoyle, undécylénoyle, lauroyle, cocoyle, palmitoyle, stéaroyle ou oléoyle.  13. A composition according to one of the preceding claims, characterized in that R-CO- represents a radical chosen from the group consisting of the propionyl, capryloyl, octanoyl, undecylenoyl, lauroyl, cocoyl, palmitoyl, stearoyl or oleoyl radical.
14. Procédé de préparation d'une composition selon l'une des revendications 1 à 11 et 13, comprenant au moins un composé de formule générale (I) et au moins un composé de formule générale (II) dans lesquelles M est l'hydrogène, ledit procédé étant caractérisé en ce qu'il comporte les étapes suivantes :  14. Method for preparing a composition according to one of claims 1 to 11 and 13, comprising at least one compound of general formula (I) and at least one compound of general formula (II) in which M is hydrogen , said method being characterized in that it comprises the following steps:
a) on fait réagir en solution aqueuse (i) un ou plusieurs composés choisis dans le groupe constitué par les acides aminés et les oligopeptides, et (ii) au moins un composé de formule (III)
Figure imgf000021_0001
a) reacting in aqueous solution (i) one or more compounds chosen from the group consisting of amino acids and oligopeptides, and (ii) at least one compound of formula (III)
Figure imgf000021_0001
dans laquelle R2, R3 et n ont les significations indiquées dans la revendication 1 et M' est un cation, in which R 2 , R 3 and n have the meanings indicated in claim 1 and M 'is a cation,
avec un dérivé activé d'un acide carboxylique de formule with an activated derivative of a carboxylic acid of formula
RCOOH, RCOOH,
b) on acidifie à un pH inférieur à 3, de préférence inférieur à 2, le milieu reactionnel formé à l'étape a)  b) the reaction medium formed in step a) is acidified to a pH of less than 3, preferably less than 2
c) on récupère ladite composition.  c) recovering said composition.
15. Procédé de préparation d'une composition selon l'une des revendications 1 à 13, comprenant au moins un composé de formule générale (I) et au moins un composé de formule générale (II) dans lesquelles M est différent de l'hydrogène, ledit procédé étant caractérisé en ce qu'il comporte les étapes suivantes :  15. Process for the preparation of a composition according to one of claims 1 to 13, comprising at least one compound of general formula (I) and at least one compound of general formula (II) in which M is different from hydrogen , said method being characterized in that it comprises the following steps:
a) on fait réagir en solution aqueuse (i) un ou plusieurs composés choisis dans le groupe constitué par les acides aminés et les oligopeptides, et (ii) au moins un composé de formule (III)
Figure imgf000022_0001
a) reacting in aqueous solution (i) one or more compounds chosen from the group consisting of amino acids and oligopeptides, and (ii) at least one compound of formula (III)
Figure imgf000022_0001
dans laquelle R2, R3, et n ont les significations indiqués dans la revendication 1 , M' étant un cation, wherein R 2 , R 3 , and n have the meanings indicated in claim 1, M 'being a cation,
avec un dérivé activé d'un acide carboxylique de formule RCOOH, with an activated derivative of a carboxylic acid of formula RCOOH,
b) on ajuste le pH du milieu reactionnel formé à l'étape a) à une valeur comprise entre 6,5 et 8, au moyen d'une base comportant le cation M,  b) the pH of the reaction medium formed in step a) is adjusted to a value between 6.5 and 8, using a base comprising the cation M,
c) on récupère ladite composition.  c) recovering said composition.
16. Un procédé selon l'une des revendications 14 et 15, caractérisé en ce que le composé de formule (III) est la sarcosine ou un sel de sarcosine.  16. A method according to one of claims 14 and 15, characterized in that the compound of formula (III) is sarcosine or a salt of sarcosine.
17. Utilisation d'une composition selon l'une des revendications 1 à 13, comme agent cosmétique ou agent destiné à l'hygiène de l'homme ou de l'animal.  17. Use of a composition according to one of claims 1 to 13, as a cosmetic agent or agent intended for human or animal hygiene.
18. Utilisation d'une composition selon l'une des revendications 1 à 13, en tant qu'agent tensio-actif.  18. Use of a composition according to one of claims 1 to 13, as surfactant.
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EP1672055A4 (en) * 2003-10-03 2006-12-13 Ajinomoto Kk Detergent compositions and processes for the production thereof
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US8765822B2 (en) 2004-12-16 2014-07-01 Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic Concentrated inverse latex, process for preparing it and industrial use thereof
WO2011030044A1 (en) 2009-09-11 2011-03-17 Société d'Exploitation de Produits pour les Industries Chimiques SEPPIC Novel powdered polymer, preparation method thereof and use of same as a thickener
WO2011138533A1 (en) 2010-05-06 2011-11-10 Societe Dexploitation De Produits Pour Les Industries Chimique Seppic Novel self-reversible reverse latex, and use thereof as a thickening agent in a cosmetic composition
US9101552B2 (en) 2010-05-06 2015-08-11 Societe Dexploitation De Produits Pour Les Industries Chimiques Seppic Self-reversible reverse latex, and use thereof as a thickening agent in a cosmetic composition
US9333162B2 (en) 2012-01-25 2016-05-10 Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic Thickening polymer reducing the stickiness of glycerine-based cosmetic formulas
WO2013110880A1 (en) 2012-01-25 2013-08-01 Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic New thickening polymer reducing the stickiness of glycerine-based cosmetic formulas
US9309342B2 (en) 2012-02-29 2016-04-12 Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic Silicone acrylate and trifluoroethyl methacrylate polymer, preparation and use thereof in cosmetics
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US10052275B2 (en) 2012-06-25 2018-08-21 Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic Surfactant-free self-reversible reverse latex, and use of same as a thickening agent in a cosmetic composition
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