Nonionic polyether surfactants

Abstract

Non-ionic polyether surfactants with improved resistance to hydrolysis are provided.

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows: 
     
         1 . A compound represented by Formula (I): 
       
         
           
           
               
               
           
         
         an isomer, a hydrate, a solvate, or a tautomer thereof, 
         wherein: 
         R is a an optionally substituted C6-C70 alkyl or optionally substituted C6-C70 alkenyl; 
         w is an integer ranging from 0 to 20, 
         x is an integer ranging from 0 to 20, 
         y is an integer ranging from 0 to 20, and 
         z is an integer ranging from 0 to 20. 
       
     
     
         2 . The compound of  claim 1 , wherein R is an unsubstituted C6-C50 alkyl or unsubstituted C6-C50 alkenyl. 
     
     
         3 . The compound of  claim 1 , wherein R is an unsubstituted C10-C25 alkyl or unsubstituted C10-C25 alkenyl. 
     
     
         4 . The compound of  claim 1 , wherein the sum of w, x, y, and z is 20. 
     
     
         5 . The compound of  claim 1 , wherein the compound is represented by Formula (IA): 
       
         
           
           
               
               
           
         
         an isomer, a hydrate, a solvate, or a tautomer thereof. 
       
     
     
         6 . The compound of  claim 1 , wherein R is n-decyl, n-undecyl, n-dodecyl, n-hexadecyl, or n-heptadecyl. 
     
     
         7 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
         or an isomer, solvate, hydrate, or a tautomer thereof, wherein x+y+x=20. 
       
     
     
         8 . The compound of  claim 1 , wherein the compound is: 
       
         
           
           
               
               
           
         
         or an isomer, solvate, hydrate, or a tautomer thereof, wherein x+y+x=20. 
       
     
     
         9 . A method of preparing of a compound of Formula (I): 
       
         
           
           
               
               
           
         
         an isomer, a hydrate, a solvate, or a tautomer thereof, 
         wherein: 
         R is a an optionally substituted C6-C70 alkyl or optionally substituted C6-C70 alkenyl; 
         w is an integer ranging from 0 to 20, 
         x is an integer ranging from 0 to 20, 
         y is an integer ranging from 0 to 20, and 
         z is an integer ranging from 1 to 20, 
         comprising the steps of: 
         (a) forming a trimethylsilyl protected derivative of compound of formula (II): 
       
       
         
           
           
               
               
           
         
       
       and
 (b) contacting the trimethylsilyl derivative of compound of formula (II) with a suitable reducing agent and gallium tribromide, optionally in a suitable solvent. 
 
     
     
         10 . The method of  claim 9 , wherein forming a trimethylsilyl derivative of compound of Formula (II) is done by contacting a compound of Formula (II) with a silylating agent in a suitable solvent. 
     
     
         11 . The method of  claim 9 , wherein the silylating agent is hexamethyldisilazane (HMDS). 
     
     
         12 . The method of  claim 9 , wherein the reducing agent is 1,1,3,3-tetramethyldisiloxane. 
     
     
         13 . The method of  claim 9 , wherein step (b) is performed at a temperature ranging from about 25° C. to about 80° C. 
     
     
         14 . The method of  claim 9 , wherein step (b) does not require a solvent. 
     
     
         15 . The method of  claim 9 , further comprising contacting the product of step (b) with water. 
     
     
         16 . A non-ionic polyether surfactant prepared by the method of  claim 9 . 
     
     
         17 . A surfactant composition comprising a compound of  claim 1 .