Novel process for preparing polyol glycosides

Abstract

A process for preparing a composition (C 1 ) represented by the formula (I): HO—CH 2 —(CHOH) n —CH 2 —O-(G) x -H, in which G represents the remainder of a reducing sugar, n is an integer equal to 2, 3 or 4 and x, which indicates the mean degree of polymerization of the remainder G, represents a decimal number greater than 1 and less than or equal to 5, characterized in that the process includes at least one step a) of reacting a polyol of formula (A 1 ): HO—CH 2 —(CHOH) n —CH 2 —OH, in which n is an integer equal to 2, 3 or 4, with a reducing sugar of formula (II): HO-G-H, in which G represents the remainder of a reducing sugar, in the presence of an acid catalyst (C a ), and in that the acid catalyst (C a ) is chosen from phosphorous acid, phosphoric acid and polyphosphoric acid.

1 . A process for the preparation of a composition (C 1 ) represented by the formula (I):
   HO—CH 2 —(CHOH) n —CH 2 —O-(G) x -H  (I),
   in which G represents the residue of a reducing sugar, n is an integer equal to 2, 3 or 4 and x, which indicates the mean degree of polymerization of said residue G, represents a decimal number greater than 1 and less than or equal to 5, characterized in that said process comprises at least one stage a) of reaction of a polyol of formula (A 1 ):
   HO—CH 2 —(CHOH) n —CH 2 —OH  (A 1 ),
 
   in which n is an integer equal to 2, 3 or 4, with a reducing sugar of formula (II):
   HO-G-H  (II)
 
   in which G represents the residue of a reducing sugar, in the presence of an acid catalyst (C a ), and in that said acid catalyst (C a ) is chosen from hypophosphorous acid, phosphoric acid and polyphosphoric acid.   
     
     
         2 . The process as defined in  claim 1 , characterized in that, in the formulae (I) and (II), said residue G of a reducing sugar is chosen from the residues of glucose, xylose and arabinose. 
     
     
         3 . The process as defined in  claim 1 , characterized in that, in the formula (I), x represents a decimal number greater than or equal to 1.05 and less than 3. 
     
     
         4 . The process as defined in  claim 1 , characterized in that, in stage a), the molar ratio, of a reducing sugar of formula (II) to polyol of formula (A 1 ), is greater than or equal to 1/6 and less than or equal to 4/1. 
     
     
         5 . The process as defined in  claim 1 , characterized in that, in stage a), the proportion by weight of acid catalyst (C a ) employed is greater than or equal to 0.05% and less than or equal to 2% per 100% of the sum of the weights of a reducing sugar of formula (II) and of polyol of formula (A 1 ). 
     
     
         6 . The process as defined in  claim 1 , characterized in that, in stage a), the acid catalyst (C a ) employed is hypophosphorous acid. 
     
     
         7 . The process as defined in  claim 1 , characterized in that, in stage a), the acid catalyst (C a ) employed is phosphoric acid. 
     
     
         8 . A composition (C 2 ) comprising, per 100% of its weight:
 from 1% to 70% by weight of a polyol of formula (A 1 ):
   HO—CH 2 —(CHOH) n —CH 2 —OH  (A 1 ),
 
   in which n is an integer equal to 2, 3 or 4;   from 25% to 98.9% by weight of a composition (C 1 ) represented by the formula (I):
   HO—CH 2 —(CHOH) n —CH 2 —O-(G) x -H  (I),
 
   
       in which G represents the residue of a reducing sugar, n is an integer equal to 2, 3 or 4 and x, which indicates the mean degree of polymerization of said residue G, represents a decimal number of greater than 1 and less than or equal to 5;
 from 0.1% to 5% by weight of a compound (B) or of a mixture of compounds (B) chosen from: 
 the compound of formula (B 11 ): 
 
       
         
           
           
               
               
           
         
         the compound of formula (B 12 ): 
       
       
         
           
           
               
               
           
         
         the compound of formula (B 13 ): 
       
       
         
           
           
               
               
           
         
         and the compound of formula (B 14 ): 
       
       
         
           
           
               
               
           
         
       
     
     
         9 . The composition (C 2 ) as defined in  claim 8 , characterized in that, in the formula (I), said residue G of a reducing sugar is chosen from the residues of glucose, xylose and arabinose and x represents a decimal number of greater than or equal to 1.05 and less than or equal to 3. 
     
     
         10 . The composition (C 2 ) as defined in  claim 8 , for which:
 in the formula (A 1 ), n is an integer equal to 2,   in the formula (I), n is an integer equal to 2, said residue G of a reducing sugar represents the residue of glucose and x represents a decimal number of between 1.05 and 2.5, and   the compound (B) is the compound of formula (B 11 ).   
     
     
         11 . The composition (C 2 ) as defined in  claim 8 , for which:
 in the formula (A 1 ), n is an integer equal to 3,   in the formula (I), n is an integer equal to 3, said residue G of a reducing sugar represents the residue of glucose and x represents a decimal number of between 1.05 and 2.5, and   the compound (B) is the compound of formula (B 12 ).   
     
     
         12 . The composition (C 2 ) as defined in  claim 8 , for which:
 in the formula (A 1 ), n is an integer equal to 4,   in the formula (I), n is an integer equal to 4, said residue G of a reducing sugar represents the residue of glucose and x represents a decimal number of between 1.05 and 2.5, and   the compound (B) is a mixture of the compound of formula (B 13 ) and the compound (B 14 ).   
     
     
         13 . A cosmetic, dermopharmaceutical or pharmaceutical formulation for topical use comprising the composition (C 2 ) as defined in  claim 8 .