Amphiphilic polymeric material

Abstract

A amphiphilic polymeric material that includes a straight or branched chain carbon-carbon backbone and a multiplicity of side chains attached to the backbone, wherein the side chains have formula (I): At least one of R 1 and R 2 is the group —C(O)Q; wherein Q includes a hydrophilic polymeric group terminated with an amine.

1 . An amphiphilic polymeric material, comprising:
 a carbon-carbon backbone derived from a homopolymer of isoprene, and   a multiplicity of side chains attached to the backbone, the side chains having a structure of formula (I):   
       
         
           
           
               
               
           
         
          where:
 R 1  and R 2  are each independently H, —C(O)WR 4 , or —C(O)Q, provided that:
 at least one of R 1  and R 2  is the group —C(O)Q; or 
 R 1  and R 2  together form a cyclic structure together with the carbon atoms to which they are attached, of formula (II): 
 
 
       
       
         
           
           
               
               
           
         
         
           R 3 , R 4 , and R 5  are each independently H or a C 1-6  alkyl group; 
           W is O or NR 4 ; 
           Q is a group of formula —NR 4 —Y—X 1 P; 
           T is a group of formula —N—Y—X 1 —P; 
           X 1  is (CH 2 ) n  or is absent; 
           n is 1-6; 
           P is H; and 
           Y is a hydrophilic polymeric group that is selected from poly(alkylene oxide), polyglycidol, poly(vinyl alcohol), poly(styrene sulphonate), or poly(acrylic acid). 
         
       
     
     
         2 . The amphiphilic polymeric material according to  claim 1 , wherein Y is a polyalkylene oxide. 
     
     
         3 . The amphiphilic polymeric material according to  claim 2 , wherein the polyalkylene oxide has a general formula (ZO) b , where:
 Z is an alkylene group having from 2 to 4 carbon atoms, and   b is an integer in a range of 1 to 125.   
     
     
         4 . The amphiphilic polymeric material according to  claim 2 , wherein the polyalkylene oxide is a random, statistical, alternating, or block copolymer, or a combination of two of these, of two or more monomer units ZO, wherein each Z is independently an alkylene group having from 2 to 4 carbon atoms. 
     
     
         5 . A method for making the amphiphilic polymeric material according to  claim 1 , the method comprising:
 reacting backbone precursors comprising pendant units of general formula (III) with side chain precursors of general formula (V) in a reaction mixture, wherein:
 formula (III) is: 
   
       
         
           
           
               
               
           
         
       
       where R 6  and R 7  are H or an acylating group, provided at least one of R 6  and R 7  is an acylating group, or R 6  and R 7  are linked to form, together with the carbon atoms to which they are attached, a group of formula (IV): 
       
         
           
           
               
               
           
         
       
       and 
       are reacted with side chain precursors of general formula (V) in a reaction mixture
 formula (V) is:
   HR 4 N—Y—X 1 H  (V); and
 
 
 allowing the amine group HR 4 N in the side chain precursors of formula (V) to react with the backbone precursors of general formula (III) or (IV) to give the amphiphilic polymeric material. 
 
     
     
         6 . The method according to  claim 5 , wherein no solvent is used. 
     
     
         7 . The method according to  claim 5 , wherein the backbone and side chain precursors are dissolved in an organic solvent during the reaction. 
     
     
         8 . The method according to  claim 5 , wherein an acid or base catalyst is added to the reaction mixture. 
     
     
         9 . The method according to  claim 5 , wherein any acylating groups which have not reacted with side chain precursors are reacted with a sodium or potassium salt.