PROCESS FOR THE PREPARATION OF A COMPOSITION OF LIPOAMINO ACIDS AND DIOLS

Abstract

Disclosed are a new composition of lipoamino acids and diols, a process for the preparation thereof, and a cosmetic or pharmaceutical composition resulting therefrom.

Claims

1. A method of making a composition (C.sub.1) comprising, per 100% of its mass: (a) - A mass proportion of greater than or equal to 50% by mass and less than or equal to 95% by mass of a compound of formula (I) or of a mixture of compounds of formula (I): ##STR00026## wherein p represents an integer greater than or equal to 5 and less than or equal to 8, Y represents either a divalent radical of formula (II.sub.a): ##STR00027## wherein R.sub.3 represents a hydrogen atom or the methyl radical, m represents an integer greater than or equal to 1 and less than or equal to 4 and R.sub.2 represents a hydrogen atom or a radical chosen from methyl, isopropyl, isobutyl, 1-methylpropyl, benzyl and 3-aminopropyl radicals; or a divalent radical of formula (II.sub.b): ##STR00028## wherein R.sub.4 represents a hydrogen atom or the hydroxyl radical and n represents an integer greater than or equal to 1 and less than or equal to 4; and X represents either the methyl radical or the methylidene radical (CH.sub.2═), or the monovalent radical of formula (III):. ##STR00029## wherein Y′ represents either the divalent radical of formula (IIa) as defined previously, or the divalent radical of formula (IIb) as defined previously, wherein when X represents the radical of formula (III), Y and Y′ are identical;. (b) - A mass proportion of greater than 0% by mass and less than or equal to 15% by mass of a diol comprising from three to eight atoms and represented either by formula (IV.sub.a):. ##STR00030## wherein each of the radicals R.sup.a.sub.1, R.sup.b.sub.1, R.sup.c.sub.1 and R.sup.d.sub.1 represent, independently of one another, a hydrogen atom or saturated aliphatic radical containing from one to five carbon atoms, or by formula (IV.sub.b):. ##STR00031## wherein t is equal to one, two or three, each of the radicals R.sup.a.sub.1, R.sup.b.sub.1, R.sup.c.sub.1, R.sup.d.sub.1, R.sup.e.sub.1 and R.sup.f.sub.1 represent,. independently of one another, a hydrogen atom or saturated aliphatic radical containing from one to five carbon atoms, wherein at least one of the radicals R.sup.a.sub.1 or R.sup.b.sub.1 and/or at least one of the radicals R.sup.c.sub.1 or R.sup.d.sub.1 do not represent a hydrogen atom;. (c) - A mass proportion of greater than or equal to 0% by mass and less than or equal to 5% by mass of a compound of formula (V) or of a mixture of compounds of formula (V): ##STR00032## wherein X represents a methyl radical or the vinyl radical (CH.sub.2═CH—), p represents an integer greater than or equal to 5 and less than or equal to 8, or of a mixture of said compounds of formula (V); and. (d) - A mass proportion of greater than 0% by mass and less than 50% by mass of water,. wherein the pH of said composition is less than or equal to 3; said method comprising: a step i) during which said diol comprising from three to eight atoms and represented either by formula (IV.sub.a) or by formula (IV.sub.b) is mixed with water to form a mixture (S.sub.1) comprising, per 100% of its mass, from 5% by mass to 70% by mass of said diol of formula (IV.sub.a) or of formula (IV.sub.b) and from 30% by mass to 95% by mass of water; a step ii) during which a compound of formula (VI.sub.a): ##STR00033## or of formula (VI.sub.b): ##STR00034## . or a mixture of at least one compound of formula (VI.sub.a) or (VI.sub.b) with at least one other compound of formula (VI.sub.a) or (VI.sub.b) is added to said mixture (S.sub.1) in a proportion such that the mixture (M.sub.1) obtained contains, per 100% of mass, from 5% by mass to 50% by mass of said compound of formula (VI.sub.a) or (VI.sub.b) or of said mixture of compounds of formula (VI.sub.a) and/or (VI.sub.b) and from 50% by mass to 95% by mass of said mixture (S.sub.1); a step iii) during which sodium hydroxide or potassium hydroxide is added to said mixture (M.sub.1) to form a mixture (M.sub.2) having a pH greater than or equal to 9; a step iv) during which an acid chloride of formula (VII): ##STR00035## wherein X and p are as defined in formula (I) above, or a mixture of acid chlorides of formula (VII), is poured into said mixture (M.sub.2), while maintaining the pH at a value greater than or equal to 9 by the joint addition of sodium hydroxide or potassium hydroxide, said step e) resulting in the formation of a mixture (M.sub.3); a step v) during which said mixture (M.sub.3) is acidified until a pH value of less than or equal to 3 is reached; a step vi) of decanting for the purpose of drawing off the mother liquors; and optionally at least one step vii) of washing with brine water to obtain, after decanting, said composition .

2. The method according to claim 1, wherein in formulae (I) and (V), X represents the methyl radical.

3. The method according to claim 1, wherein, in formula (I), the divalent radical Y represents the divalent radical of formula (II.sub.a1): ##STR00036## wherein m represents an integer greater than or equal to one and less than or equal to four and R.sub.2 represents a hydrogen atom or a radical chosen from methyl, isopropyl, isobutyl, 1-methylpropyl, benzyl or 3-aminopropyl radicals.

4. The method according to claim 3, wherein, in formula (I), the divalent radical Y represents the divalent radical of formula (II′.sub.a1): ##STR00037## .

5. The method according to claim 4, wherein, in formulae (I) and (V), the monovalent radical X—(CH.sub.2).sub.p—C(═O)— represents the octanoyl radical.

6. The method according to claim 2, wherein, in formulae (I) and (V), the monovalent radical X—(CH.sub.2).sub.p—C(═O)— represents the 10-undecylenoyl radical and Y represents the divalent radical of formula (II.sub.a2): ##STR00038## .

7. The method according to claim 1, wherein said diol comprising from three to eight atoms and represented either by formula (IVa) or by formula (IVb) is selected from the group consisting of 1,2-propanediol, 1,2-butanediol, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-octanediol, 2,3-butanediol, 2,3-pentanediol, 2,3-hexanediol, 2,5-hexanediol and 2-methyl-2,4-pentanediol.

8. The method according to claim 7, wherein said diol comprising from three to eight atoms and represented either by formula (IV.sub.a) or by formula (IV.sub.b) is chosen from 1,2-propanediol, 1,2-butanediol, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol or 2-methyl-2,4-pentanediol.

9. A method of making a cosmetic, dermocosmetic, dermopharmaceutical or pharmaceutical composition for topical use (C) comprising a mass proportion of greater than or equal to 5% by mass and less than or equal to 30% by mass of a compound of formula (I′) or of a mixture of compounds of formula (I′): ##STR00039## wherein X represents a methyl radical or the vinyl radical (CH.sub.2═CH—), p represents an integer greater than or equal to 5 and less than or equal to 12, M.sup.+ represents the sodium cation, Y represents either a divalent radical of formula (II.sub.a): ##STR00040## wherein R.sub.3 represents a hydrogen atom or the methyl radical, m represents an integer greater than or equal to 1 and less than or equal to 4 and R.sub.2 represents a hydrogen atom or a radical chosen from methyl, isopropyl, isobutyl, 1-methylpropyl, benzyl and 3-aminopropyl radicals; or a divalent radical of formula (II.sub.b): ##STR00041## wherein R.sub.4 represents a hydrogen atom or the hydroxyl radical and n represents an integer greater than or equal to 1 and less than or equal to 4; and X represents either the methyl radical or the methylene radical (CH.sub.2═), or the monovalent radical of formula (III): ##STR00042## wherein Y′ represents either the divalent radical of formula (II.sub.a) as defined above, or the divalent radical of formula (IIb) as defined above, wherein, when X represents the radical of formula (III), Y and Y′ are identical; (b) - A mass proportion of greater than 5% by mass and less than or equal to 30% by mass of a diol comprising from three to eight atoms and represented either by formula (IV.sub.a): ##STR00043## wherein each of the radicals R.sup.a.sub.1, R.sup.b.sub.1, R.sup.c.sub.1 and R.sup.d.sub.1 represent, independently of one another, a hydrogen atom or saturated aliphatic radical containing from one to five carbon atoms, or by formula (IV.sub.b): ##STR00044## wherein t is equal to one, two or three, each of the radicals R.sup.a.sub.1, R.sup.b.sub.1, R.sup.c.sub.1, R.sup.d.sub.1, R.sup.e.sub.1 and R.sup.f.sub.1 represent, independently of one another, a hydrogen atom or saturated aliphatic radical containing from one to five carbon atoms, it being understood that at least one of the radicals R.sup.a.sub.1 or R.sup.b.sub.1 and at least one of the radicals R.sup.c.sub.1 or R.sup.d.sub.1 do not represent a hydrogen atom; (d) - A mass proportion of greater than 40% by mass and less than 90% by mass of water, it being understood that the pH of said composition (C) is less than or equal to 9 and greater than or equal to 5.5, said method comprising a step viii), during which are simultaneously or sequentially added to the composition (C.sub.1) as defined in claim 1, the necessary amounts of diol of formula (IVa) or of formula (Vb), in aqueous sodium hydroxide solution and in water, until the proportions and pH value as defined above are reached .

10. The method according to claim 9, wherein in formulae (I) and (V), X represents the methyl radical.

11. The method according to claim 9, wherein, in formula (I), the divalent radical Y represents the divalent radical of formula (II.sub.a1): ##STR00045## wherein m represents an integer greater than or equal to one and less than or equal to four and R.sub.2 represents a hydrogen atom or a radical chosen from methyl, isopropyl, isobutyl, 1-methylpropyl, benzyl or 3-aminopropyl radicals .

12. The method according to claim 11, wherein, in formula (I), the divalent radical Y represents the divalent radical of formula (II.sub.a1): ##STR00046## .

13. The method according to claim 12, wherein, in formulae (I) and (V), the monovalent radical X—(CH.sub.2).sub.p—C(═O)— represents the octanoyl radical.

14. The method according to claim 10, wherein, in formulae (I) and (V), the monovalent radical X—(CH.sub.2).sub.p—C(═O)— represents the 10-undecylenoyl radical and Y represents the divalent radical of formula (II.sub.a2): ##STR00047## .

15. The method according to claim 9, wherein said diol comprising from three to eight atoms and represented either by formula (IVa) or by formula (IVb) is selected from the group consisting of 1,2-propanediol, 1,2-butanediol, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-octanediol, 2,3-butanediol, 2,3-pentanediol, 2,3-hexanediol, 2,5-hexanediol and 2-methyl-2,4-pentanediol.

16. The method according to claim 15, wherein said diol comprising from three to eight atoms and represented either by formula (IV.sub.a) or by formula (IV.sub.b) is chosen from 1,2-propanediol, 1,2-butanediol, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol or 2-methyl-2,4-pentanediol.

Description

DESCRIPTION OF THE PREFERRED EMBODIMENTS

Preparation of Compositions (C.SUB.1.) According to the Invention

[0110] The common procedure is as follows: [0111] Introducing, at ambient temperature and with mechanical stirring, 20% by mass of glycocoll (glycine) into 80% by mass of a mixture of water/diol (85/15 by mass), [0112] Adding 30% sodium hydroxide to achieve a pH of approx. 10, [0113] Gradually pouring in octanoyl chloride (0.9 molar equivalent), while maintaining the pH at approximately 10 with 30% sodium hydroxide, at a temperature of 18 to 36° C., [0114] Breaking with 37% hydrochloric acid qs to achieve a pH of approx. 2, [0115] Drawing off the mother liquors at 60° C., [0116] Washing with 5% brine water, [0117] Decanting and drawing off at 65° C.

[0118] The features of the compositions (C.sub.1) are collated in table 1 below:

Preparation of a Comparative Composition (C.SUB.21.)

[0119] Introducing, at ambient temperature and with mechanical stirring, 20% by mass of glycocoll (glycine) into 80% by mass of a mixture of water/diol (85/15 by mass), [0120] Adding 30% sodium hydroxide to achieve a pH of approx. 10, [0121] Gradually pouring in lauroyl chloride (0.9 molar equivalent), while maintaining the pH at approximately 10 with 30% sodium hydroxide, at a temperature of 18 to 36° C., [0122] Breaking with 37% hydrochloric acid qs to achieve a pH of approx. 2, [0123] Drawing off the mother liquors at 60° C., [0124] Washing with 5% brine water, [0125] Decanting and drawing off at 65° C.

[0126] The features of the composition (C.sub.21) thus obtained are collated in table 2 below.

Preparation of a Comparative Composition (C.SUB.22.)

[0127] Introducing, at ambient temperature and with mechanical stirring, 20% by mass of a mixture of glycine, L-aspartic acid, L-glutamic acid and L-alanine, in the mass proportions of glycine/L-aspartic acid/L-glutamic acid/L-alanine of 10%/35%/45%/10% per 100% by mass of said mixture of amino acids, into 80% by mass of a mixture of water/diol (85/15 by mass), [0128] Adding 30% sodium hydroxide to achieve a pH of approx. 10, [0129] Gradually pouring in lauroyl chloride (0.9 molar equivalent), while maintaining the pH at approximately 10 with 30% sodium hydroxide, at a temperature of 18 to 36° C., [0130] Breaking with 37% hydrochloric acid qs to achieve a pH of approx. 2, [0131] Drawing off the mother liquors at 60° C., [0132] Washing with 5% brine water, [0133] Decanting and drawing off at 65° C. [0134] The features of the composition (C.sub.22) thus obtained are collated in table 2 below.

TABLE-US-00001 (C.sub.1A) (C.sub.1B) (C.sub.1C) Diol (IV.sub.a) or (IV.sub.b) 2-methyl-2,4- pentanediol 1,2-propanediol 1,3-propanediol Content of diol (IV.sub.a) or (IV.sub.b) 8.9% by mass 1.2% by mass 1.1% by mass Content of octanoic acid (V) 0.8% by mass 2.2% by mass 3.9% by mass Water content 19.0% by mass 19.8% by mass 16.0% by mass Content of N-octanoyl glycine (I) 71.3% by mass 76.8% by mass 78.5% by mass Presence of by-products No No 0.5% by mass pH of the composition pH = 1.8 pH = 2.0 pH = 1.9 (C.sub.1D) (C.sub.1E) (C.sub.1F) Diol (IV.sub.a) or (IV.sub.b) 1,2-butanediol 1,3-butanediol 1,4-butanediol Content of diol (IV.sub.a) or (IV.sub.b) 8.1% by mass 3.8% by mass 0.9% by mass Content of octanoic acid (V) 0.6% by mass 2.4% by mass 3.0% by mass Water content 19.1% by mass 20.2% by mass 23.0% by mass Content of N-octanoyl glycine (I) 72.2% by mass 73.6% by mass 71.9% by mass Presence of by-products No No 1.2% by mass pH of the composition pH = 1.6 pH = 1.5 pH = 1.7 Content of diol (IV.sub.a) or (IV.sub.b) 6.6% by mass 2.2% by mass 10.1% by mass Content of octanoic acid (V) 0.8% by mass 2.9% by mass 0.6% by mass Water content 19.0% by mass 18.5% by mass 16.2% by mass Content of N-octanoyl glycine (I) 73.6% by mass 74.6% by mass 73.1% by mass Presence of by-products No 1.8% by mass No pH of the composition pH = 1.8 pH = 2.1 pH = 2.2

TABLE-US-00002 (C.sub.21) (C.sub.22) Diol (IV.sub.a) or (IV.sub.b) 1,2-propanediol 1,2-propanediol Content of diol (IV.sub.a) or (IV.sub.b) 0.9% by mass 1.9% by mass Content of lauric acid (V) 4.1% by mass 12.9% by mass Water content 11.0% by mass 27.5% by mass Content of N-lauroyl glycine (I) 83.2% by mass 11.9% by mass Content of N-lauroyl alanine (I) - 11.0% by mass Content of N-lauroyl aspartic acid (I) - 12.2% by mass Content of N-lauroyl glutamic acid (I) - 20.4% by mass Presence of by-products 0.8% by mass 2.2% by mass pH of the composition pH = 2.1 pH = 2.2

[0135] Analysis of the compositions (C.sub.1A), (C.sub.1B) and (C.sub.1D), (C.sub.1E) and (C.sub.1G), which are subjects of the present invention, reveals that they do not contain by-products, unlike the compositions (C.sub.1C), (C.sub.1F), (C.sub.21) and (C.sub.22), and that their fatty acid concentration is lower than those of the compositions (C.sub.1C), (C.sub.1H), (C.sub.1F), (C.sub.21) and (C.sub.22).