Functionalized quaternary ammonium halides and use thereof

Abstract

Various embodiments relate generally to the preparation of functional quaternary ammonium salts. More particularly, various embodiments relate to the preparation of hydroxyl group functionalized quaternary ammonium halides. Various embodiments also relate to the preparation of photocurable quaternary ammonium halides from the hydroxyl group functionalized quaternary ammonium halides. In other embodiments, preparation of hydrolytically curable quaternary ammonium halide derivatives by a sol-gel process is also disclosed. Said hydroxyl group functionalized quaternary ammonium halides are useful for making polymers, which are useful as water insoluble, non-leaching, active by contact antifouling materials.

1 . A quaternary ammonium halide of Formula (I) 
       
         
           
           
               
               
           
         
         wherein: 
         X is Br or Cl; 
         R is selected from the group consisting of C 1 -C 20  alkyl, C 6 -C 14  aryl, C 3 -C 8  heteroaryl, C 3 -C 20  cycloalkyl, and C 7 -C 20  aralkyl; 
         R′ is selected from the group consisting of C 1 -C 20  alkyl, C 3 -C 20  cycloalkyl, C 7 -C 20  aralkyl, and C 2 -C 15  alkenyl. 
       
     
     
         2 . The quaternary ammonium halide of  claim 1 , wherein R′ is C 1 -C 20  alkyl. 
     
     
         3 . The quaternary ammonium halide of  claim 2 , wherein R′ is 
       
         
           
           
               
               
           
         
       
     
     
         4 . The quaternary ammonium halide of  claim 1 , wherein R′ is C 7 -C 20  aralkyl. 
     
     
         5 . The quaternary ammonium halide of  claim 4 , wherein R′ is 
       
         
           
           
               
               
           
         
       
     
     
         6 . The quaternary ammonium halide of  claim 1 , wherein R is C 1 -C 20  alkyl. 
     
     
         7 . A method of making the quaternary ammonium halide of Formula (I) of  claim 1 , comprising:
 reacting a tertiary amino primary alcohol with a dihaloaliphatic compound or a dihaloaralkyl compound.   
     
     
         8 . The method of  claim 7 , wherein the tertiary amino primary alcohol is N—N-dimethylaminoethanol. 
     
     
         9 . The method of  claim 7 , wherein the dihaloaliphatic compound is 1,10-dichlorodecane. 
     
     
         10 . The method of  claim 7 , wherein the dihaloaralkyl compound is α,α′-dibromo-m-xylene. 
     
     
         11 . The quaternary ammonium halide of  claim 6 , wherein R is