Preparation of polysaccharide betainate type compounds, compounds obtained, their use and compositions comprising them

Abstract

A process for preparing compounds from the polysaccharide betainate family, novel compounds so obtained, and their use in. cosmetics or in dermatology, as well as the compositions, such as cosmetic or dermatological compositions, comprising said novel compounds.

1 . A process for preparing a compound of formula (I):  
     
       
         
         
             
             
         
       
     
     in which: 
 R 1 , R 2 , and R 3 , which may be identical or different, are chosen from linear and branched, saturated and unsaturated C 1 -C 30  hydrocarbon radicals optionally interrupted by at least one hetero atom chosen from N, O, and S and/or optionally substituted with at least one radical chosen from —OH, halogen and C 6 -C 22  aryl radicals;  
 A is chosen from linear and branched, saturated and unsaturated divalent C 1 -C 22  hydrocarbon radicals, optionally interrupted by at least one hetero atom chosen from N, O, and S, and/or optionally substituted with at least one hydroxyl radical;  
 X −  is an anion deriving from an acid chosen from mineral and organic acids; and  
 Y is a polysaccharide residue;  
 comprising: 
 reacting a polysaccharide with an N,N-dialkylaminocarboxylic acid of formula (II):  
                     
 
 in the presence of at least one reaction activator; and quaternizing the ester formed using a quaternization agent.  
 
   
   
       2 . The process according to  claim 1 , wherein the reaction between the polysaccharide and the N,N-dialkylaminocarboxylic acid is carried out in a polar aprotic solvent.  
   
   
       3 . The process according to  claim 2 , wherein said polar aprotic solvent is chosen from at least one of dimethylsulphoxide (DMSO) and dimethylformamide.  
   
   
       4 . The process according to  claim 1 , wherein the quaternization agent is chosen from halides and sulphates.  
   
   
       5 . The process according to  claim 4 , wherein the halides are chosen from chlorides, iodides and bromides.  
   
   
       6 . The process according to  claim 4 , wherein the halides are chosen from C 1 -C 30  alkyl halides.  
   
   
       7 . The process according to  claim 6 , wherein the halides are a methyl iodide (Mel).  
   
   
       8 . The process according to  claim 4 , wherein the sulphates are chosen from C 1 -C 30  alkyl sulphates.  
   
   
       9 . The process according to  claim 8 , wherein the sulphates are a methyl sulphate (Me 2 SO 4 ).  
   
   
       10 . The process according to  claim 1 , wherein the quaternization is carried out at a temperature ranging from about 20° C. to about 70° C.  
   
   
       11 . The process according to  claim 10 , wherein the quaternization is carried out at a temperature ranging from about 22° C. to about 27° C.  
   
   
       12 . The process according to  claim 1 , wherein the N,N-dialkylaminocarboxylic acid is chosen from at least one of N,N-dimethylglycine (N,N-dimethylaminoacetic acid), N,N-dimethyl-.beta.-aminopropanoic acid, N,N-dimethyl-.gamma.-aminobutanoic acid, N,N-dimethyl-5-aminopentanoic acid, and N,N-dimethylbenzylamine carboxylic acid.  
   
   
       13 . A process for preparing a compound of formula (I):  
     
       
         
         
             
             
         
       
     
     in which: 
 R 1 , R 2 , and R 3 , which may be identical or different, are chosen from linear and branched, saturated and unsaturated C 1 -C 30  hydrocarbon radicals optionally interrupted by at least one hetero atom chosen from N, O, and S and/or optionally substituted with at least one radical chosen from —OH, halogen and C 6 -C 22  aryl radicals;  
 A is chosen from linear and branched, saturated and unsaturated divalent C 1 -C 22  hydrocarbon radicals, optionally interrupted by at least one hetero atom chosen from N, O, and S, and/or optionally substituted with at least one hydroxyl radical;  
 X −  is an anion deriving from an acid chosen from mineral and organic acids; and  
 Y is a polysaccharide residue;  
 comprising: 
 reacting a polysaccharide with a salt of an N,N,N-trialkylammoniocarboxylic acid of formula (III):  
                     
 
 wherein the reaction is carried out in a polar aprotic solvent; and the reaction takes place in the presence of at least one reaction activator.  
 
   
   
       14 . The process according to  claim 13 , wherein the polar aprotic solvent is chosen from at least one of dimethylsulphoxide (DMSO) and dimethylformamide.  
   
   
       15 . The process according to  claim 13 , wherein said salt of an N,N,N-trialkylammoniocarboxylic acid is chosen from at least one of salts of N,N,N-trimethylammonioacetic acid, N,N,N-trimethyl-.beta.-ammoniopropa-noic acid, N,N,N-trimethyl-.gamma.-ammoniobutanoic acid, N,N,N-trimethyl-5-ammoniopentanoic acid, and N,N,N-trimethyl-benzylammoni-ocarboxylic acid.  
   
   
       16 . The process according to  claim 13 , wherein said salt is chosen from citrates, lactates, tartrates, halides, and sulphates.  
   
   
       17 . The process according to  claim 16 , wherein said halides are chosen from chlorides, bromides, and iodides.  
   
   
       18 . The process according to  claim 13 , wherein said at least one reaction activator is chosen from carbodiimides, hydroxybenzotriazole, and 4-dimethylaminopyridine.  
   
   
       19 . The process according to  claim 18 , wherein the carbodiimides are a N,N′-diisopropylcarbodiimide.  
   
   
       20 - 67 . (canceled)  
   
   
       68 . The process according to  claim 1 , wherein said at least one reaction activator is chosen from carbodiimides, hydroxybenzotriazole, and 4-dimethylaminopyridine.  
   
   
       69 . The process according to  claim 68 , wherein the carbodiimides are a N,N′-diisopropylcarbodiimide.