Composition of lipoamino acids and alkanediols, process for the preparation thereof, and cosmetic or pharmaceutical composition resulting therefrom

Abstract

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

Claims

1. A composition (C.sub.1) comprising, per 100% of 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):
X—[CH.sub.2].sub.p—C(═O)—Y—OH  (I), in which p represents an integer greater than or equal to 10 and less than or equal to 20, Y represents either a divalent radical of formula (II.sub.a):
—[N(R.sub.3)—CH(R.sub.2)—C(═O)—].sub.m—  (II.sub.a), in which R.sub.3 represents a hydrogen atom or a 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): ##STR00010## in which R.sub.4 represents a hydrogen atom or a hydroxyl radical and n represents an integer greater than or equal to 1 and less than or equal to 4; and X represents either a methyl radical or a monovalent radical of formula (III):
HO—Y′—C(═O)—  (III), in which 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 25% by mass of a linear or branched alkanediol containing from six to eight carbon atoms; (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):
X—[CH.sub.2].sub.p—C(═O)—OH  (V), in which X represents a methyl radical, p represents an integer greater than or equal to 10 and less than or equal to 20, or a mixture of said compounds of formula (V); and (d) —a mass proportion greater than 0% by mass and less than or equal to 50% by mass of water, it being understood that the pH of said composition is less than or equal to 3.

2. The composition (C.sub.1) as defined in claim 1, wherein, in formulae (I) and (V), X represents a methyl radical.

3. The composition (C.sub.1) as defined in claim 2, wherein in formula (I), the divalent radical Y represents the divalent radical of formula (II.sub.a1):
—[NH—CH(R.sub.2)—C(═O)—].sub.m—  (II.sub.a1), in which 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 composition (C.sub.1) as defined in claim 3, wherein in that in formula (I), the divalent radical Y represents the divalent radical of formula (II′.sub.a1):
—NH—CH.sub.2—C(═O)—  (II′.sub.a1).

5. The composition (C.sub.1) as defined in claim 3, wherein in formula (I), the divalent radical Y represents the divalent radical of formula (II′.sub.a2):
—NH—CH[—CH(CH.sub.3)—CH.sub.2—CH.sub.3]—C(═O)—  (II′.sub.a2).

6. The composition (C.sub.1) as defined in claim 1, wherein in formulae (I) and (V), the monovalent radical X—(CH.sub.2).sub.p—C (═O)— represents the palmitoyl radical.

7. The composition (C.sub.1) as defined in claim 1, wherein said diol containing from six to eight carbon atoms is chosen from 1,6-hexanediol, 1,2-hexanediol, 2-methyl 2,4-pentanediol or 1,2-octanediol.

8. A method for preparing the composition (C.sub.1) as defined in claim 1, comprising the following successive steps: a step a) during which said alkanediol containing from six to eight carbon atoms is mixed with water to form a mixture (S.sub.1) containing, per 100% of mass, from 5% by mass to 70% by mass of said alkanediol and from 30% by mass to 95% by mass of water; a step b) during which a compound of formula (VI.sub.a): ##STR00011## or of formula (IV.sub.b): ##STR00012## 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 c) 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 d) during which an acid chloride of formula (VII):
X—[CH.sub.2].sub.p—C(═O)—Cl  (VII), in which 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 e) during which said mixture (M.sub.3) is acidified until a pH of less than or equal to 3 is reached; a step f) of decantation for the purpose of drawing off the mother liquors; at least one step g) of washing with brined water to obtain, after decantation, said desired composition.

9. A method for preparing 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′):
X—[CH.sub.2].sub.p—C(═O)—Y—O.sup.−M.sup.+  (I′), in which X represents a methyl radical, p represents an integer greater than or equal to 10 and less than or equal to 20, M.sup.+ represents a sodium cation, Y represents either a divalent radical of formula (II.sub.a):
—[N(R.sub.3)—CH(R.sub.2)—C(═O)—].sub.m—  (II.sub.a), in which R.sub.3 represents a hydrogen atom or a 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): ##STR00013## in which R.sub.4 represents a hydrogen atom or a hydroxyl radical and n represents an integer greater than or equal to 1 and less than or equal to 4; and X represents either a methyl radical or a monovalent radical of formula (III):
HO—Y′—C(═O)—  (III), in which Y′ represents either the divalent radical of formula (II.sub.a) as defined previously, or the divalent radical of formula (IIb) as defined previously, it being understood that 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 linear or branched alkanediol containing from six to eight carbon atoms; (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 h), during which the necessary quantities of linear or branched alkanediol containing from six to eight carbon atoms, of aqueous sodium hydroxide solution and of water are added simultaneously or sequentially to the composition (C.sub.1) as defined in claim 1 to obtain the proportions and pH value as defined above.

10. A method for preparing the composition (C.sub.1) as defined in claim 1, comprising the following successive steps: —a step a) during which said alkanediol containing from six to eight carbon atoms is mixed with water to form a mixture (S.sub.1) containing, per 100% of mass, from 5% by mass to 70% by mass of said alkanediol and from 30% by mass to 95% by mass of water; a step b) during which a compound of formula (VI.sub.a): ##STR00014## or of formula (IV.sub.b): ##STR00015## 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 its 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 c) 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 d) during which an acid chloride of formula (VII):
X—[CH.sub.2].sub.p—C(═O)—Cl  (VII), in which 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 e) during which said mixture (M.sub.3) is acidified until a pH of less than or equal to 3 is reached; and a step f) of decantation for the purpose of drawing off the mother liquors.

11. The composition (C.sub.1) as defined in claim 2, wherein in formulae (I) and (V), the monovalent radical X—(CH.sub.2).sub.p—C(═O)—represents the palmitoyl radical.

12. The composition (C.sub.1) as defined in claim 3, wherein in formulae (I) and (V), the monovalent radical X—(CH.sub.2).sub.p—C(═O)—represents the palmitoyl radical.

13. The composition (C.sub.1) as defined in claim 4, wherein in formulae (I) and (V), the monovalent radical X—(CH.sub.2).sub.p—C(═O)—represents the palmitoyl radical.

14. The composition (C.sub.1) as defined in claim 5, wherein in formulae (I) and (V), the monovalent radical X—(CH.sub.2).sub.p—C(═O)—represents the palmitoyl radical.

15. The composition (C.sub.1) as defined in claim 2, wherein said diol containing from six to eight carbon atoms is chosen from 1,6-hexanediol, 1,2-hexanediol, 2-methyl 2,4-pentanediol or 1,2-octanediol.

16. The composition (C.sub.1) as defined in claim 3, wherein said diol containing from six to eight carbon atoms is chosen from 1,6-hexanediol, 1,2-hexanediol, 2-methyl 2,4-pentanediol or 1,2-octanediol.

17. The composition (C.sub.1) as defined in claim 4, wherein said diol containing from six to eight carbon atoms is chosen from 1,6-hexanediol, 1,2-hexanediol, 2-methyl 2,4-pentanediol or 1,2-octanediol.

18. The composition (C.sub.1) as defined in claim 5, wherein said diol containing from six to eight carbon atoms is chosen from 1,6-hexanediol, 1,2-hexanediol, 2-methyl 2,4-pentanediol or 1,2-octanediol.

19. The composition (C.sub.1) as defined in claim 6, wherein said diol containing from six to eight carbon atoms is chosen from 1,6-hexanediol, 1,2-hexanediol, 2-methyl 2,4-pentanediol or 1,2-octanediol.

20. A method for preparing the composition (C.sub.1) as defined in claim 2, comprising the following successive steps: a step a) during which said alkanediol containing from six to eight carbon atoms is mixed with water to form a mixture (S.sub.1) containing, per 100% of mass, from 5% by mass to 70% by mass of said alkanediol and from 30% by mass to 95% by mass of water; a step b) during which a compound of formula (VI.sub.a): ##STR00016## or of formula (IV.sub.b): ##STR00017## 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 c) 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 d) during which an acid chloride of formula (VII):
X—[CH.sub.2].sub.p—C(═O)—Cl  (VII), in which 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 e) during which said mixture (M.sub.3) is acidified until a pH of less than or equal to 3 is reached; a step f) of decantation for the purpose of drawing off the mother liquors; at least one step g) of washing with brined water to obtain, after decantation, said desired composition.

Description

DESCRIPTION OF THE PREFERRED EMBODIMENTS

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

(2) The common procedure is as follows:

(3) Introduction, at ambient temperature and with mechanical stirring, of 20% by mass of isoleucine into 80% by mass of a mixture of water/diol (80/20 by mass), Addition of 30% sodium hydroxide to achieve a pH of approx. 11.5, Gradual flow of palmitoyl chloride (0.8 molar equivalent), while maintaining the pH at approximately 11-12 with 30% sodium hydroxide, at a temperature of 20 to 40° C., Breaking up with 37% hydrochloric acid q.s. to achieve a pH of approx. 2, Drawing off of mother liquors at 60° C., Washing with 5% brined water, Decantation and drawing off at 60° C.

(4) The features of compositions (C.sub.1) are collated in table 1 below:

(5) TABLE-US-00001 TABLE 1 (C.sub.1A) (C.sub.1B) (C.sub.1C) Diol Hexylene glycol 1,2-Hexanediol 1,6-Hexanediol (IV.sub.a) or (IV.sub.b) Diol content 10.2% by mass 20.1% by mass 3.9% by mass Palmitoic acid 2.1% by mass 2.0% by mass 1.3% by mass content (V) Water content 11.8% by mass 6.3% by mass 7.1% by mass N-Palmitoyl isoleucine 75.9% by mass 71.6% by mass 87.7% by mass content (I) Presence of byproducts No No No pH 1% 2.7 2.3 2.5 (C.sub.1D) Diol 1,2-Octanediol (IV.sub.a) or (IV.sub.b) Diol content 22.4% by mass (IV.sub.a) or (IV.sub.b) Octanoic acid 2.2% by mass content (V) Water content 17.6% by mass N-Octanoyl glycine 57.8% by mass content (I) Presence of byproducts No pH of the composition 2.1
Preparation of a Comparative Composition (C.sub.21) Introduction, at ambient temperature and with mechanical stirring, of 20% by mass of glycocoll (glycine) into 80% by mass of a mixture of water/diol (85/15 by mass), Addition of 30% sodium hydroxide to achieve a pH of approx. 10, Gradual flow of 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., Breaking up with 37% hydrochloric acid q.s. to achieve a pH of approx. 2, Drawing off of mother liquors at 60° C., Washing with 5% brined water, Decantation and drawing off at 65° C. The features of the composition (C.sub.21) thus obtained are collated in table 2 below.

(6) Preparation of a Comparative Composition (C.sub.22) Introduction, at ambient temperature and with mechanical stirring, of 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), Addition of 30% sodium hydroxide to achieve a pH of approx. 10, Gradual flow of 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., Breaking up with 37% hydrochloric acid q.s. to achieve a pH of approx. 2, Drawing off of mother liquors at 60° C., Washing with 5% brined water, Decantation and drawing off at 65° C. The features of the composition (C.sub.22) thus obtained are collated in table 2 below.

(7) TABLE-US-00002 TABLE 2 (C.sub.21) (C.sub.22) Diol 1,2-Propanediol 1,2-Propanediol (IV.sub.a) or (IV.sub.b) Diol content 0.9% by mass 1.9% by mass (IV.sub.a) or (IV.sub.b) Lauric acid 4.1% by mass 12.9% by mass content (V) Water content 11.0% by mass 27.5% by mass N-Lauroyl glycine 83.2% by mass 11.9% by mass content (I) N-Lauroyl alanine — 11.0% by mass content (I) N-Lauroyl aspartic acid — 12.2% by mass content (I) N-Lauroyl glutamic acid — 20.4% by mass content (I) Presence of byproducts 0.8% by mass 2.2% by mass pH of the composition pH = 2.1 pH = 2.2
The analysis of the compositions (C.sub.1A), (C.sub.1B), (C.sub.1C) and (C.sub.1D), the subject of the present invention, shows that they contain no byproducts and that their fatty acid concentration is minimal, whereas the comparative compositions (C.sub.21) and (C.sub.22) prepared in the presence of 1,2-propanediol are characterized by a higher content of residual fatty acids and by the presence of byproducts.