Polysiloxane block copolymers

Abstract

This invention encompasses novel amphiphilic block copolymers comprising polysiloxane blocks and polycationic blocks. The polycationic blocks are formed from diallyldialkylammonium derivatives. The formed block copolymers are particularly useful for treating or conditioning keratinous substances such as hair or skin.

1 . An amphiphilic block copolymer comprising at least
 a) siloxane polymer block of formula (I)   
       
         
           
           
               
               
           
         
         wherein n is a number between 2 and 10,000, 
         and 
         b) a cationic polymer block formed from at least a cationic monomer of formula (II) 
       
       
         
           
           
               
               
           
         
         wherein R 3  and R 4  are independently of one another hydrogen or C 1 -C 4  alkyl; R 5  and R 6  are, independently, hydrogen or an alkyl, hydroxyalkyl, carboxyalkyl, carboxyamidalkyl or alkoxyalkyl groups having from 1 to 18 carbon atoms; and Y −  represents an anion. 
       
     
     
         2 . An amphiphilic block copolymer according to  claim 1 , wherein the siloxane polymer block is a polymer of formula (I) 
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  are independently alkyl, alkoxy, phenylalkyl, aryl, aryloxy, alkylaryl, alkylamine, alkylhydroxy, polyoxyalkylene and polyalkylene polyamine, n is a number between 2 to 10,000. 
     
     
         3 . An amphiphilic block copolymer according to  claim 1 , wherein the cationic monomer of formula II is selected form the group of monomers consisting of diallyldimethylammonium chloride (DADMAC), diallyidiethylammonium chloride, diallyldimethylammonium bromide, diallyldimethylammonium sulfate, diallydimethylammonium phosphate, diallyidi(beta-ethoxyethyl)ammonium chloride and diallyidi(beta-hydroxyethyl)ammonium chloride. 
     
     
         4 . An amphiphilic block copolymer according to  claim 1 , wherein the cationic polymer block is formed from at least a cationic monomer of formula (II) and a second cationic monomer selected from the group consisting of ammonium or quaternary salts of dialkyl amino alkyl (meth)acrylates and dialkyl amino alkyl (meth)acrylamides. 
     
     
         5 . An amphiphilic block copolymer according to  claim 4 , wherein the second cationic monomer is dimethylaminoethyl acrylate methyl chloride quaternary salt, dimethylaminoethyl acrylate methyl sulfate quaternary salt, dimethyaminoethyl acrylate benzyl chloride quaternary salt, dimethylaminoethyl acrylate sulfuric acid salt, dimethylaminoethyl acrylate hydrochloric acid salt, dimethylaminoethyl methacrylate methyl chloride quaternary salt, dimethylaminoethyl methacrylate methyl sulfate quaternary salt, dimethylaminoethyl methacrylate benzyl chloride quaternary salt, dimethylaminoethyl methacrylate sulfuric acid salt, dimethylaminoethyl methacrylate hydrochloric acid salt, diethylaminoethyl acrylate, diethylaminoethyl acrylate methyl chloride quaternary salt, diethylaminoethyl methacrylate, diethylaminoethyl methacrylate methyl chloride quaternary salt, methacrylamidopropyltrimethylammonium chloride, acrylamidopropyltrimethylammonium chloride, dimethylaminopropylacrylamide methyl sulfate quaternary salt, dimethylaminopropylacrylamide sulfuric acid salt or dimethylaminopropylacrylamide hydrochloric acid salt. 
     
     
         6 . An amphiphilic block copolymer according to  claim 1 , wherein Y −  is selected from the group of anions consisting of chloride, bromide, iodide, substituted or unsubstituted aryl sulfonates, sulfate, alkyl sulfonates such as methyl sulfonate, ethyl sulfonate, carboxylates, nitrate, phosphates, tetrafluoroborate, tetraalkylborate, tetraarylborate, perchlorate, and hexafluorophosphate. 
     
     
         7 . An amphiphilic block copolymer according to  claim 1 , wherein the amphiphilic block copolymer is linear, grafted, star or comb block copolymer. 
     
     
         8 . An amphiphilic block copolymer according to  claim 1 , wherein the amphiphilic block copolymer is a diblock or triblock amphiphilic block copolymer. 
     
     
         9 . An amphiphilic block copolymer according to  claim 1 , wherein the amphiphilic block copolymer is water soluble or water dispersible. 
     
     
         10 . An amphiphilic block copolymer according to  claim 1 , wherein the weight ratio of the siloxane polymer block to cationic polymer block varies from about 1:100 to about 100:1. 
     
     
         11 . An amphiphilic block copolymer of formula III 
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , n and Y −  are as defined in  claim 2  and x is an integer between 2 and 1000 and L is a linking group. 
     
     
         12 . The amphiphilic block copolymer according to  claim 11 , wherein the linking group contains sulfur. 
     
     
         13 . The amphiphilic block copolymer according to  claim 11  wherein formula (III) is 
       
         
           
           
               
               
           
         
       
       and x is 1-10. 
     
     
         14 . A hair conditioning shampoo composition comprising:
 a) an amphiphilic block copolymer according to  claim 1 ,   and   b) a detersive surfactant.   
     
     
         15 . A hair conditioning shampoo composition according to  claim 14 , further comprising a starch. 
     
     
         16 . A hair conditioning shampoo composition according to  claim 15 , wherein the starch is cationic. 
     
     
         17 . The composition according to  claim 14 , wherein the detersive surfactant is nonionic, anionic, cationic, zwitterionic or any mixtures thereof. 
     
     
         18 . The composition according to  claim 14 , wherein the surfactant is anionic. 
     
     
         19 . Preparation of an amphiphilic block copolymer according to  claim 1 , said preparation comprising the steps of polymerizing the cationic monomer of formula (II) 
       
         
           
           
               
               
           
         
         wherein R 3  and R 4  are independently of one another hydrogen or C 1 -C 4  alkyl; R 5  and 
         R 6  are, independently, hydrogen or an alkyl, hydroxyalkyl, carboxyalkyl, carboxyamidalkyl or alkoxyalkyl groups having from 1 to 18 carbon atoms; and Y −  represents an anion, 
         in the presence of a siloxane block polymer of formula (I) 
       
       
         
           
           
               
               
           
         
         wherein n is a number between 2 and 10,000, 
         and 
         an initiator, 
         wherein the siloxane block polymer is terminated with a chain transfer group. 
       
     
     
         20 . A method of conditioning a keratinous substrate by applying the amphiphilic block copolymer according to  claim 1  onto the substrate.