MXPA96004924A - 2,3-dihydroxypropyl-2-(1-oxoalkyl)amino-2-desoxyglyco-pyrano sides, a process for their preparation and use - Google Patents

Abstract

The invention is related to compounds of fórmula (I);wherein, R denotes a lineal or branched, saturated or unsaturated alkyl group, containing from 5 to 21 carbon atoms;the invention also refers to a process for aforementioned compounds preparation, characterized in that it consist of, a) forming a N-acylglycosamine of glycosamine hydrochloride and C6-C22 acid chloride, and b) reacting compound of stage a) with glycerol inpresence of an acid catalyst;it also refers to detergent or cosmetic compositions including aforementioned compounds.

Description

2. 3-DIHYDROXYPROPYL-2- (1-OXOfl-CALYL) RMINO-2- DESOXIGLUCOPIRPHLNOSIDES, A PROCEDURE FOR YOUR PREPARATION AND USE The present invention relates to the field of neutral surfactants. More particularly, it refers to 2,3-d-hydroxypropyl-2- (l -oxoalkyl) arnino-2-deoxy-glucopyranosides, to the process of their preparation, to compositions containing said compounds and to their use. In the field of surfactants there is a continuous search for compounds free of toxic and irritant nature, especially, namely, the skin and mucosae of the user with which they have contact, being additionally necessary for said compounds to preserve the environment. Surfactants are found in applications in sectors as diverse as cosmetology, hair care and detergency in an industrial environment. They are generally used in the form of compositions which, apart from their main function, must henceforth have an ever increasing number of specific properties. A shampoo, for example, is not only sought after for its detergent properties, but also for its antidandruff activity, its ability to condition the hair, to prevent itching and to impart a pleasant sensation. To achieve this goal, a first option It consists in using one or several surfactants + ivoe neu + ros jun + o with agents that exhibit the required properties. Neutral surfactants, which generally e are polyoxyethylenates (B. Hefford, urfac + ant Surveillance, SPC, pp. 35-36, Nov. 1991), and polyalkyl glycosides derived from glucose, therefore have been proposed (EP-R-569 682; Siracusa, Happi, pp. 100-108, April 1992, J. Thiern and T. Boc er, Special Publication of the Royal Society of Chernistry, vol 107, pp. 123-147, 1992. P. Schulz, Chi ica Oggi, pp. 33-38, August-September 1992, D. Balzer, Tensi e, Surf, Vol. 28 No. 6, pp. 419-426, 1991, B. Salka, Cosrnetics a Toiletpes, vol. 108, pp. 89-94, March 1993). The aforementioned surfactants have in common a good detergency and ba irritation to the or, in addition, the polyalkyl glucosides being biodegradable. However, their main disadvantage is that they are difficult to formulate, due to their limited sputtering capacity and / or large number of surfactants in the composition. Therefore, said agents can be used only in a small amount, since a washing base and foam consisting of an ammonium surfactant has to be added thereto. The irritant nature of the latter has to be quenched by the addition of a third amphoteric surfactant. Rdernás, because the poliox? Efr i leñados compounds are subject to contain 1,4-d? Oxano, which is suspected of having a Carcinogenic action, it is likely that the degree to which they are incorporated will increase in the future. On the other hand, polyalkyl glucides are obtained in the form of mixtures that result from intermolecular and / or intramolecular isoerization and oligomerization phenomena. Accordingly, the formulation of compositions containing said surfactants is misleading. A second option is to limit the number of surfactants by using surfactants that have specific properties. Said agents have been described in particular by Ernmerling (Polym, Bull., Vol.6, pp. 305-308, 1992) and Jnouye et al. (3. R. Chem. Soc. Vol.78, pp. 2825-2832, 1956 ). Are alkyl glucosamine compounds, especially N-acyl glucosarnine, of the type exhibiting specific properties such as radiation protection (DE 2708667 and US 4,323,561)? the diagnosis and transport of surfactants through the formation of vesicles (WO 91/04013 and UO 88/06883), the treatment of allergies, acne or dermatitis (EP-fl-209 770), munoestirnulante activity (Vallaní et al. , Rrzneim Forsch, Vol 39 No. 10, pp. 1190-1195, 1989), hair growth stimulation (EP-FL-348 184) and antimicrobial activity (3. Rm Oil Chemists' Soc. 1), pp. 17-22, 1993 and JP 03112905). The main disadvantage of the agents mentioned above is their low solubility in water which, as a result, limits its use. There is little hope of overcoming this disadvantage by converting it into chloride (3.ROCS, vol 70 (1), pp. 1 7-22 1993 and 3P61-57321) or into hydrobromide, because its irritant nature characterizes most of the cationic surfactants are then introduced. Rhora new neutral surfactants have been found, characterized because they correspond to the formula: wherein R denotes a branched or linear, saturated or unsaturated alkyl group containing from 5 to 21 carbon atoms. The invention relates in particular to compounds of the formula (I) wherein the radical R contains from 7 to 17 carbon atoms and, even better from 9 to 13. In the present description the compounds of the formula (I) are called 2,3-d? Hydroxypyrrol- (2- (l-oxoalkyl) ammo-2-deoxyglucopyranosides? The invention also relates to a process for the preparation of the compounds of the formula (I), this process being characterized because it consists of: a) forming an N-acylglycosine hydrochloride of glucoseinin and C6-C22 acid chloride, and b) reacting the compound of step a) with glycerol in the presence of an acid catalyst. The glucosamine hydrochloride of the process according to the invention is generally obtained by means of conventional methods for acid hydrolysis of quntma. The acid chloride of the process according to the invention is chosen C6-C22 acid chlorides and preferably Cß-Ciß acid chlorides having a branched or linear, saturated or unsaturated alkyl radical, with the exception of the mdecylenic acid chloride. This chloride can be prepared in particular by reaction of the corresponding acid with thionyl chloride at a temperature of 60-70 ° C and distillation at a reduced pressure of the acid chloride obtained. The acid catalyst of the process according to the invention is selected from the group consisting of acids in general, for example hydrochloric or sulfuric acid, an alkylsulphobic acid + as as decyl- or lauryl sulfuric acid, a sulphonic acid such as benzenesulfonic acid , paratoluensulonic or camphorsulphonic, an alkylsulphonic acid such as ethansulic acid, deculonulonic acid, sulfuric acid or sulfosuccinic acid, an alkyl phospholipid such as decyl or lupulic acid, a perhalohydric acid such as perchloric acid, acid hydrophosphorous or mixtures of these acids, and resins in H + form such as sulphonic resins and acid clays.

Preferably it employs sulfuric acid, rnetansulonic acid, succinic acid or an alkyl? L-fosuccin +, or hypophosphorous acid and mixtures of these acids. Step a) of the process according to the invention consists in reacting the acid chloride and glucosamine hydrochloride in a molar ratio which is generally between 0. 7 and 1.3 and preferably between 0.9 and 1.1. In general, glucosamine hydrochloride is dissolved in aqueous sodium hydroxide at a concentration between 6 and 50 g / liter and preferably 2.5 and 17.5 g / liter. The concentration of glucosamine hydrochloride in the solution is generally between 0.2 and 1 mole equivalent / liter and preferably 0.25 and 0.5 mole equivalent / liter. The acid chloride in a sodium hydroxide solution with a normality between 1 and 10 and preferably 2 to 6 are added simultaneously to the already prepared glucose hydrochloride solution. fll adding acid chloride is generally carried out at a flow rate between 5 and 500 rnl / hour and preferably 10 and 100 rnl / hour. The flow rate of the sodium hydroxide solution is adapted so that the pH of the reaction mixture is between 6 and 11 and preferably 8 and 10.5. The temperature of the reaction mixture is generally between 0 and a ° C and preferably 10 and 50 ° C.

The reaction mixture is preferably maintained at 50 to 800 revolutions / nm and at least 10 (3 and 400 revolutions / m, especially with the aid of a double knife device.) After adding the acid chloride, the reaction can continue at the aforementioned temperature and the stirring conditions for a period can vary from 0.25 to 24 hours and preferably from 0.5 to 6 hours. After the end of the reaction, the pH of the reaction mixture is adjusted to a value between 4 and 8 and preferably 5 and 7 by adding an acid to form a precipitate. It is obvious that any type of acid known to one skilled in the art can be used. Sulfuric acid, methansulonic acid, succinic acid, an alkyl sulfosuccinate, hypophosphorous acid and mixtures of these acids are advantageously employed. The precipitate of the aforementioned reaction mixture can be recovered in two ways. According to a first alternative form, the precipitate is recovered by draining and washing continuously with water. In accordance with a second alternative form, the precipitate is recovered by filtering the reaction mixture, draining, washing one to four times, and preferably two to three times, with 0.1 to 2 liters and preferably 0.2 to one liter of water, and Drain one more time.

The precipitate obtained at the end of the step < < ) comprises N-acylgl ucosami na. Step (b) of the process according to the invention the aforementioned N-acylglucosamine precipitate is reacted with glycerol in the presence of an acid catalyst. Glycerol is generally used in the process, so that the ratio of the number of molar equivalents of glycerol to the number of molar equivalents of N-acylglucosamine is between 1 and 50 and preferably and 30. In general, when the acid catalyst as defined above is an acid, the ratio of the number of molar equivalents of the acid to a number of molar equivalents of N-acylglucosamine is between 10-3 and preferably 10-2 g. -? . When this catalyst is a resin or a clay, the amount used, expressed as weight equivalent calculated on the basis of one molar equivalent of N-acylglucosamine, is between 0.05 and 6. When a dehydration effect is sought, a dehydration agent conventional such as a molecular sieve- or a zeolite can optionally be added to the reaction mixture. The reaction is generally carried out at a pressure between 0.13 and 101. 32 kP, preferably 0.013 and 39.49 r- 'Pa, at a temperature between 25 and 200 ° C, preferably 80 and 105 ° C, and for a period that can vary from 0.25 to 24 hours, preferably 1 to 12 hours. At the end of the reaction, the catalyst is removed by filtration. When it is an acid, it is initially converted into a salt of the corresponding acid, for example by adding a solution of sodium hydrogencarbonate. For the purpose of facilitating the filtration step optionally it is possible to employ a solvent selected from ethers, for example tet rahydrofuran, ethylene glycol dirnethyl ether, halogenated hydrocarbons, for example dichloromethane and dichloroethane and chloroform, esters, for example ethyl acetate, propylacetate , and butylacetate, alcohols, for example methanol, ethanol and propanol, solvents of the amide type, for example N-rne-lformamide and N, Nd? rnet? lforrnarn? da, and mixtures of these solvents. Preferably an alcohol is used. Therefore, the obtained reaction mixture is a solution of 2,3-d? H? Drox? Prop? L-2- (l-oxoalqu? L) am? No-2-deso? -glucocapyranoside in glycerol, which it is generally in the form of a mixture of the anomers a and ß in position 1, the ratio of the anomer to relative to the anomer ß being preferably between 80/20 and 90/10. The anoneros cr and ß optionally can be separated, for example by means of chromatography on a silica column. 2, 3-d? H? Drox? Prop? L-2- (1-oxoalkyl) am? No-2-deoxy? -glucopyranoside according to the invention has excellent properties of foaming, moisture, dispersion, ul sifi cation and soli bilization and, in addition, has an anti-dandruff activity, the ability to soften and tone the skin, and the possibility of forming vesicles for the stabilization and transport of active ingredients . The compounds according to the invention are particularly recommended for preparing detergent compositions which are especially designed for the industrial, or cosmetic, environment. These compositions, which are also the subject of the present invention, may only contain one of the compounds of the formula (I) or a mixture of said compounds. The detergent compositions according to the invention are characterized in that they comprise from 0.1 to 60% and preferably from 10 to 40% by weight of 2,3-dihydroxypropyl-2- (1-oxoalkyl) amine-2 deoxyglucanositol and from 40 to 99.9% and preferably 60 to 90% by weight of a detergent base and / or an adjuvant. The detergent base is generally selected from ammonium, nonionic, cationic or amphoteric surfactants and mixtures of these compounds. The adjuvant is generally selected from adjuvants or mixtures of adjuvants which are known in the field of liquids or washing axle powders, especially zeolites and complexes for calcium and magnesium. The cosmetic compositions that are the lerna do la invention are characterized in that they comprise from 0.1 to 50% and preferably from 5 to 35% by weight of 2, 3-d? h? drox? propyl? - (l ~ oxoalkyl) arnmo-2 ~ deoxyglucoposterioside and from 50 to 99.9% and preferably from 55 to 95% by weight of an excipient and / or detergent base and / or an adjuvant. The cosmetic compositions may be in the form of a soft liquid soap, shampoo, bath foam, bath gel or a care formula, especially an ointment, cream and milk to beautify. When the composition is a mild liquid soap, it contains from 5 to 30% by weight, and preferably from 5 to 20%, of 2,3-dihydroxypropyl-2- (1-oxoalkyl) arnino-2-deoxyglucopyranoside and from 70 to 95% and preferably from 80 to 95% by weight of an excipient. The excipient is generally selected from anionic surfactants such as sodium cocoylisthionate, sodium lauryl sulfate or the sodium salt of an alkylpyrid, amphoteric surfactants such as alkylaminopropyl betaine, and in particular cocoamidopropylbetaine, heavy mineral oils, cellulose derivatives such such as carboxymethyl cellulose, solvents such as alcohols and more particularly ethanol or propylene glycol, complexes such as EDTR, sodium chloride, fatty alcohols such as cetyl alcohol, preserving agents, perfumes, dyes and mixtures of these compounds. When the composition according to the invention A shampoo, especially a mild shampoo for frequent use, a mild anti-dandruff shampoo, a treatment shampoo or one with hair-conditioning effect, preferably contains 5 to 35% by weight of a detergent base containing from 10 to 75 % by weight of 2, 3-d? hydroxylpropyl-2- (1-oxoalkyl) arnmo-2-deoxyglucopyranoside and from 65 to 95% by weight of an adjuvant. The detergent base is generally selected from alkyl ether sulphates such as sodium or magnesium laurethyl sulfate, alkyl ether sulfate p > ethanol, such as polyoxie lauple-sulphate, sodium-filled, alkylbetaines such as cocoylbetaine, alkylated idopropylbetaines such as cocoylaminopropylbetaines, a betaine of alkyldi ethylammonoacetic acid such as lauryl-dimethylamino acid betaine, alkylamine and hydroxypropyl amine sulfobetaine, sodium or -olieisulphonates, alkylpolyethylene glycols such as octadecyl-PEG 15, alkynrnidazole, such as cocoylimidazoliurnhetama, ethersul fosuccmates to the cholines such as disodium lauryl ether, lauryl phosuccinate, β-alkylammopropionates such as sodium β-lauryllaminopropionate, alkylamide, inetilglycoses such as launlalquil-sodium diarrhea glycol and mixtures of these compounds. The adjuvant is generally selected from thicknesses, texture agents such as diethanolamides of fatty acid, especially cocoyldiethanolarnide, and to the chelated silica, particularly the hydropylate, sodium chloride, dialkylcarboxylates of ethylene glycol, more particularly ethylene glycol distearate, fatty amine oxides, more particularly N-cocoyl oxide, whose compounds are generally used in a proportion of 0-10% by weight. The adjuvant can also be selected from conditioning agents, emollients such as wheat protein hydrolysates and cellulose ethers containing quaternary ammonium (nitrogen content: 1-3%, molecular weight: 50-150 00), copolymers of Acplamide / dimethylalkyl-arnomide chloride (0.5-5% by weight), complexes such as EDTR and galactipic acid (0.1-1% by weight), perfumes, pearlizing agents, preservatives, acidifying agents, water and mixtures of these compounds . When the composition according to the invention is a bath foam, it preferably contains from 5 to 35% by weight of a detergent base containing more than 50% by weight of 2,3-d? H? Drox? Prop? L2 - (l-oxoaqu? l) am? no-2-deoxyribonucleic acid-surfactant and from 65 to 95% by weight of an adjuvant. The detergent base is generally chosen from compounds that are known to the person skilled in the art. Examples that may be mentioned are alkylenidobetaines such as cocoyl idopropylbetaine, sorbitan alkylcarboxylates ethoxylate such as ethoxylated sorbitan laurate and mixtures of these compounds. The adjuvant is generally chosen from mono- or t-tatanolates of fatty acid (0-10% by weight), dialkylcarbonylates of ethoxylated propylene glycol (0.5% by weight). weight), polyethylene glycols such as tolyethylene glycol (0-5% by weight), alkylacrylics such as oleylacrylics (0-5% by weight), vegetable oils such as sweet almond oil (0-10% by weight), sodium chloride , EDTR (0-5% by weight), fatty alcohols such as hexadecanol (0-2% by weight), preservatives, perfumes, dyes, water and mixture of these compounds. When the composition according to the invention is a bath gel, it preferably contains from 5 to 35% by weight of a detergent base containing at least 50% by weight of 2,3-dihydropropyl 2 (l). -oxoalkyl) amino-2-deoxy? gluco? anó-been and from 65 to 95% by weight of an adjuvant. The detergent base is generally selected from polyoxyethylethenylated alkylsulfosuccinates such as cocoylsul osuccinate containing 3 moles of ethylene oxide, N-alkylaryn glycinates, ammonium alkyl sulfates such as ammonium lauryl amides and mixtures of these compounds. The adjuvant is generally selected from ethoxylated propylene glycol alkylcarboxylates such as ethoxylated propylene glycol dioleate (0-5% by weight), alkylenidebetaines such as α-rilamidopropylbetaine (0-5% by weight), pearlescent agents (0-7% by weight) ), acrylic gels (0-1% by weight), sodium chloride, complex agents, preserving agents, per-fumes, purified water and mixtures of these compounds. Finally, the composition in accordance with the invention can be a facial care formulation, especially an ointment, a cream or a trim milk, having a gel-like structure. The examples below allow illustrating the invention, however, without limiting it. In these examples, the following measurement methods are used: The foaming capacity is measured by means of bubbling nitrogen at a constant speed (1 1 / h) through an inlay (water permeability: 0.11 l / h) placed in the base of a test tube with thermostat and graduated (32 rnrn x 210 m) containing 20 nl of an aqueous solution containing 3 g / 1 of 2,3-d? hydroxypropyl 2 - (1-oxoacyl) ammon? 2 -deoxyglucopyrioside and 12 g / 1 glycerol. The amount of foam generated by means of bubbles (1 minute and 40 seconds) is calculated volumetrically immediately after the bubbling stops. The volume of the foam thus formed is expressed in me. The wetting capacity is in accordance with the test consisting in monitoring for 600 seconds the amount of solution to be tested (3 g of active substances per liter of glycerol, 25 QC) absorbed by an unbleached cotton cloth ( 2.5 cm x cm; 0.145 g, according to the NF standard T73-406 (December 1975), the piece of cloth slipped on the surface of the surfactant solution and the drag generated by the capillary increase of the solution is continuously registered (automatic Kruss voltage meter equipped with K 121 absorption software). The mass absorbed by the fabric is measured during saturation (MS, in g) and the time necessary to reach saturation (TS, in s). The decrease in the surface tension of the water is measured by conventional tension measurement according to the modified ISO 304 model in that the dimensions of the rectangular plate are 25 rnm x 5 mm x 0.1 rnrn. The surface tension t is expressed in rnN / rn. The examples below allow the invention to be illustrated, however, without limiting it.

EXAMPLES 1 to 6 R 21.57 g (0.10 moles) of glucosarnine idrate chlorine (G, 220-6; Rldrich), dissolved in 200 nl in an aqueous solution of sodium hydroxide (0.5N) at 20 ° C are added, at a rate of 1 rnl / rnin and with (100 revolutions / mm; shaft with a double blade) stirring 20.3 g of acid chloride of the following acids: octanoic (Example 1; Rldpch Ref. 0.473-3), decanoic (Example 2; flldrich Ref. 14,029-5), indecanoic (Example 1, Rldrich Ref. 24,943-2), indecilic (Example 4; Aldrich Ref. 16,166-7), dodecanoic (Example 5; Rldrich Ref. 15,693-0) or tetradecanoic (Example 6; Ref. 29,861-1) and, simul- taneously, a 4N solution of sodium hydroxide, for adjust and maintain the pH to 9.5. After 2 hours of further stirring, the pH is adjusted to 6 by adding an aqueous solution of methanesulfonic acid in a concentration of 70% by weight. A precipitate, which is filtered, drained, washed twice with 60 ml of water and once drained, is formed in a conventional glass filter. Therefore, the precipitate obtained is a mixture of the o and ß anomers of the corresponding 2- (l-oxoalkylamine-2-deoxyglucopyranose, whose yield, based on the dry material, is shown in Table 1. 10 g of the precipitate obtained before, are in contact with 51.3 g (0.557 mol) of glycerol (13,487-2, flldrich) and 0.48 g (5 x 10-3 mol) of methanesulfonic acid with agitation (300 revolutions / in) for 4 hours, 110 ° C and under a vacuum of 30 Hg. The clear reaction mixture, thus obtained, is cooled to 40 ° C, diluted with 500 ml of absolute ethanol and the pH is adjusted to 6 by adding powdered sodium hydrogencarbonate. The obtained mixture is filtered (embedded glass) and the filtrate is concentrated in a rotary evaporator (vacuum: 2.5 kPa, temperature: 60 ° C) .Therefore, an oil is recovered that contains the anomers a and ß of 1 2 , 3-dihi droxipropí 1-2 - (1-oxoalquilo) amino-2-desox? Gicopiranos? Corresponds corresponien e (20% in weight in glyce ol). The obtained ceite is analyzed by means of thin layer chromatography (TLC) on a silica plate graft (RP18; Merck) eluted with a mixture of 75:25 v: v MeOH / H ?O. The migration spots are developed with the help of a solution of sulfuric acid at a concentration of 50% in water and heated at 120 ° C for 2 minutes. A stain in elongated form is observed whose RF value is shown in table 1. The physicochemical characteristics of the aforementioned oil are shown in table 1.

TABLE 1 * Alqu? Lpol? Glucos? Do (Henkel Ref. APG 1200) It was found that the spurnability of the compounds of Examples 4, 2 and 5 is greater than or equal to that of the APG, the reference product in this case.

It has been found that the foam formed during the measurement of the foaming capacity is stable and that the decrease in the volume of the foam is greater than 20% after 20 minutes (examples 1 and 6). The a and b anomers of the oil according to example 4 are separated by flash chromatography (35-70 μm silica column, length: 25 cm, diameter 5.6 crn, eluent: CHCl 3 then CHCl 3 / MeOH, refractorne detection). The anomers a and ß therefore obtained are characterized by means of the following analytical methods: - thin-layer chromatography: identical RF equal to 0.6 in the case of each anomer (silica plate, thickness: 200 μm, particle size: 5 -10 μ; eluent 8: 2 v: v CHCl 3 / MeOH); high performance liquid chromatography (HPLC): retention time (RT) equal to 17.4 min and 14.7 rnin respectively (RP18 Lichrospher column, diameter: 4 rnm, length 125 rnm, particle size: 5 μm, eluent 50:50 v : v MeOH / H2?, flow rate: 1 ml / rnin, detection: UV (\: 220 nrn) and differential refractometer, - IR spectroscope (1% KBr disc: vOH: 3350 crní; ORCH2; 2853 and 2825 crn *; VCO-NH2: 624 and 1552 crn *; -13C NMR 200 MHz: pyridine-ds: anonero a Chemical change Carbon (pprn) Cl 99.22 - 99.02 C2 55.48 C3 71.71 C4 74.31 C5 82.31 C6 70.55 (CH2) n 36.59 - 33.95 29.58 29.26 - 29.04 26.24 CO 174.40 Cl '62.59 - 62.04 C2' 72.89 - 72.67 C3 '64.62 - 64.44 -CH = CH2 139.32 -CH-CH2 114.52 year ß Chemical change Carbon (pprn) CO 174.84 Cl 103.04 C2 57.38 OR

Claims (5)

NOVELTY OF THE INVENTION CLAIMS 1. - Compound of the formula: wherein R denotes a branched or linear, saturated or unsaturated alkyl group, containing from 5 to 21 carbon atoms. 2. The compound in accordance with the claim 1, further characterized in that the radical R contains from 7 to 17 carbon atoms. 3. The process for the preparation of the compound according to any of claims 1 and 2, further characterized in that it consists of, a) forming a N-acyl glucosamine glucosamine hydrochloride and C6-C22 acid chloride and b) react the compound of step (a) with glycerol in the presence of an acid catalyst. 4. The process according to claim 3, further characterized in that the molar ratio of chloride hydrochloride / gl? Thing ina acid is between 0.7 and 00

1. 3. The method according to any of claims 3 and 4, further characterized in that the ratio of the number of molar equivalents of glycerol to the number of molar equivalents of N-acylglucosamine of the stage (b) is between 1 and 50. 6. The process according to one of claims 3 to 5, further characterized in that the catalyst is selected from the group consisting of acids, resins in the form of H * and acid clays. 7. The process according to claim 6, further characterized in that the ratio of the number of molar equivalents of the acid to the number of molar equivalents of N-acylglucosamine is between 10-3 and i. 8. The process according to claim 6, further characterized in that the amount of resin or clay, expressed as weight equivalent calculated on the basis of a molar equivalent of N-acylglucosarnin, is between 0.05 and 6. 9.- The detergent composition characterized in that it includes from 0.1 to 60% by weight of the compound according to any of claims 1 and 2, and from 40 to 99.9% by weight of a detergent base and / or an adjuvant. 10. The cosmetic composition characterized in that it includes from 0.1 to 50% by weight of the compound according to any of claims 1 and 2, and from 50 to 99.9% in weight of an excipient and / or of a detergent base and / or an adjuvant. 11. The composition according to claim 10, further characterized in that it belongs to the group consisting of soft liquid soaps, shampoos, bath foams, bath gels and care formulations, especially ointments, creams and embellishing milks. 1

2. The use of the compound according to any of claims 1 and 2, as a surfactant. 1

3. The use of the compound according to any of claims 1 and 2, as a washing base. 1

4. The use of the compound according to any of claims 1 and 2, as anti-dandruff agent. 1

5. The use of the compound according to any of claims 1 and 2, as a hair conditioning agent.