New lysine derivatives containing an Ne-alkoxy or Ne-alkenoxycarbonyl group, their preparation and their use in cosmetic, pharmaceutical, hygiene or food compositions

Abstract

Lysine derivatives, salts of the derivatives, their optical isomers of D or L configuration, or their mixtures, the derivatives containing an N e -alkoxy or N e -alkenoxycarbonyl group and having the formula: in which: R represents a linear or branched C 8 -C 24 alkyl radical or alkenyl radicals, are used in cosmetic, pharmaceutical, hygiene or food compositions, particularly compact compositions.

1 . Lysine derivatives containing an N e -alkoxy or N e -alkenoxycarbonyl group of formula:  
       
         
           
           
               
               
           
         
       
       in which: 
 R represents a linear or branched C 13 -C 24 , alkyl radical, the C 16  radical being branched, or a linear or branched C 8 -C 24  alkenyl radical, and the salts of the said compounds of formula (I) as well as their optical isomers of D or L configuration or their mixtures.  
 
     
     
         2 . Lysine derivatives according to    claim 1   , characterized in that the said salts are salts of inorganic or organic cations.  
     
     
         3 . Lysine derivatives according to either of claims  1  and  2 , characterized in that they are chosen from the group consisting of N e -2-hexyldecyloxycarbonyl-L-lysine, N e -2-decyltetradecyloxycarbonyl-L-lysine and N e -tetradecyloxycarbonyl-L-lysine.  
     
     
         4 . Lysine derivatives according to any one of the preceding claims, characterized in that the said derivatives have a melting point greater than 250° C. and have a particle size of between 10 nm and 500 μm and preferably between 0.1 and 25 μm.  
     
     
         5 . Process for the preparation of the lysine derivatives of formula (I) as defined according to any one of the preceding claims, characterized in that it consists in reacting lysine or one of its salts, of known configuration, in aqueous medium and at basic pH, with a solution of a copper salt, in then reacting the solution of the copper complex thus obtained, of formula:  
       
         
           
           
               
               
           
         
       
       with a compound of formula:  
       
         
           
           
               
               
           
         
       
       in which: 
 R is as defined according to    claim 1   ,  
 and X is chosen from the group consisting of a chlorine atom, a chloromethyl radical and an imidazolyl radical, the said compound of formula (III) being added without solvent, and  
 in treating the copper salt of the N e -substituted lysine thus obtained with a decomplexing agent and, optionally, in purifying the compound obtained.  
 
     
     
         6 . Preparation process according to    claim 5   , characterized in that the said copper salt solution is a copper sulphate solution.  
     
     
         7 . Preparation process according to either of claims  5  and  6 , characterized in that the decomplexing agent is an aqueous solution of the disodium salt of ethylenediaminetetraacetic acid.  
     
     
         8 . Cosmetic, pharmaceutical, hygiene or food composition, characterized in that it contains a lysine derivative corresponding to the following formula:  
       
         
           
           
               
               
           
         
       
       in which: 
 R represents a linear or branched C 8 -C 24  alkyl or alkenyl radical, and the salts of the said compounds of formula (I′) as well as their optical isomers of D or L configuration or their mixtures.  
 
     
     
         9 . Composition according to    claim 8   , characterized in that the lysine derivative of formula (I′) is chosen from the group consisting of N e -2-ethylhexyloxycarbonyl-L-lysine, N e -dodecyloxycarbonyl-L-lysine, N e -hexadecyloxycarbonyl-L-lysine, N e -decyloxycarbonyl-L-lysine, N e -2-butyloctyloxycarbonyl-L-lysine, N e -2-hexyldecyloxycarbonyl-L-lysine, N e -2-decyltetradecyloxycarbonyl-L-lysine and N e -tetradecyloxycarbonyl-L-lysine.  
     
     
         10 . Composition according to    claim 8    or    9   , characterized in that the said lysine derivative is present in a proportion of between 0.05% and 80% by weight with respect to the total weight of the composition.  
     
     
         11 . Composition according to any one of    claims 8    to    10   , characterized in that the said lysine derivative is present in a proportion of between 1% and 30% by weight with respect to the total weight of the composition.  
     
     
         12 . Composition according to any one of    claims 8    to    11   , characterized in that it additionally contains at least one additive chosen from the group consisting of surface-active agents, fatty substances, organic solvents, silicones, thickeners, emollients, sunscreening agents, treating agents, anti-foaming agents, moisturizing agents, fragrances, preservatives, anti-oxidizing agents, sequestrants, flavouring agents, basifying or acidifying agents, fillers and inorganic or organic powders.  
     
     
         13 . Use of a lysine derivative corresponding to the formula (I′) according to claims  8  and  9  as substance for coating substrate particles.  
     
     
         14 . Use of a lysine derivative according to    claim 13   , characterized in that the substrate particles are chosen from optionally coloured insoluble fillers.  
     
     
         15 . Use of a lysine derivative according to    claim 14   , characterized in that the said fillers are chosen from metal oxides or zinc, iron, titanium, manganese, cerium and/or zirconium, and their nanopigments, or nylon, polyethylene, mica or talc powders.