Process for preparing water-soluble polyhydroxyaminoether

Abstract

A water soluble polymer comprising a copolyhydroxyaminoether having side-chains of polyalkylene oxides, an aqueous solution of said polymer and process for preparing the copolyhydroxyaminoether.

1 . A process for preparing a water-soluble polymer which comprises (1) reacting an equivalent or excess of a difunctional amine or mixtures thereof with an excess or equivalent amount of a diglycidyl ether of a bisphenol or mixtures thereof in the presence of water, optionally in the presence of a monofunctional nucleophile and optionally in the presence of a catalyst; or (2) reacting an equivalent or excess of a difunctional amine or mixtures thereof with an excess or equivalent amount of a diglycidyl ether of a bisphenol or mixtures thereof in the presence of water, optionally in the presence of a monofunctional nucleophile which functions as a terminating agent and, optionally, in the presence of a catalyst; or (3) dissolving in water an amine selected from primary amine, a bis(secondary) diamine, or a mono-amine-functionalized poly(alkylene oxide) or mixtures thereof, adding to the amine solution a diglycidyl ether in an amine hydrogen equivalent to epoxide equivalent ratio of from 0.9:1 to 1.2:1 under conditions sufficient to cause the amine moieties to react with the epoxy moieties to form a polymer backbone having amine linkages, ether linkages and pendant hydroxyl moieties.  
   
   
       2 . The process according to  claim 1  wherein the water soluble polymer is prepared by reacting an equivalent or excess of a difunctional amine or mixtures thereof with an excess or equivalent amount of a diglycidyl ether of a bisphenol or mixtures thereof in the presence of water, optionally in the presence of a monofunctional nucleophile and optionally in the presence of a catalyst.  
   
   
       3 . The process according to  claim 2  wherein the monofunctional nucleophile is present and is selected from a secondary amine, hydrogen sulfide, ammonia, ammonium hydroxide, a monofunctional phenol, an aryloxide salt, a carboxylic acid, a carboxylic acid salt, a mercaptan, or thiolate salt.  
   
   
       4 . The process according to  claim 2  wherein the monofunctional nucleophile is present and is selected from diethanolamine, N-(2-hydroxyethyl)piperazine, piperadine, diethylamine, dipropylamine, or dibenzylamine.  
   
   
       5 . The process according to  claim 2  wherein the monofunctional nucleophile is present and is selected from phenol, acetic acid or propanoic acid, and the catalyst is present and is selected from a phosphonium or ammonium salt.  
   
   
       6 . The process according to  claim 1  wherein the water soluble polymer is prepared by reacting an equivalent or excess of a difunctional amine or mixtures thereof with an excess or equivalent amount of a diglycidyl ether of a bisphenol or mixtures thereof in the presence of water, optionally in the presence of a monofunctional nucleophile which functions as a terminating agent and, optionally, in the presence of a catalyst.  
   
   
       7 . The process according to  claim 1  wherein the water soluble polymer is prepared by dissolving in water an amine selected from primary amine, a bis(secondary) diamine, or a mono-amine-functionalized poly(alkylene oxide) or mixtures thereof, adding to the amine solution a diglycidyl ether in an amine hydrogen equivalent to epoxide equivalent ratio of from 0.9:1 to 1.2:1 under conditions sufficient to cause the amine moieties to react with the epoxy moieties to form a polymer backbone having amine linkages, ether linkages and pendant hydroxyl moieties.  
   
   
       8 . The process according to  claim 1  wherein the difunctional amine is ethanolamine or a primary amine having the formula:  
     
       
         
         
             
             
         
       
       wherein R 5  is hydrocarbyl, R 6  is hydrogen, methyl, hydrocarbyl or mixtures thereof, and q is about 1 to about 1000; the diglycidyl ether of a bisphenol is the diglycidyl ether of bisphenol A.  
     
   
   
       9 . The process according to  claim 2  wherein the difunctional amine is ethanolamine or a primary amine having the formula:  
     
       
         
         
             
             
         
       
       wherein R 5  is hydrocarbyl, R 6  is hydrogen, methyl, hydrocarbyl or mixtures thereof, and q is about 1 to about 1000; the diglycidyl ether of a bisphenol is the diglycidyl ether of bisphenol A.  
     
   
   
       10 . The process according to  claim 1  wherein the difunctional amine is ethanolamine or a primary amine having the formula:  
     
       
         
         
             
             
         
       
       wherein R 5  is hydrocarbyl, R 6  is hydrogen, methyl, hydrocarbyl or mixtures thereof, and q is about 1 to about 1000; the diglycidyl ether of a bisphenol is the diglycidyl ether of bisphenol A.  
     
   
   
       11 . The process according to  claim 3  wherein the difunctional amine is ethanolamine or a primary amine having the formula:  
     
       
         
         
             
             
         
       
       wherein R 5  is hydrocarbyl, R 6  is hydrogen, methyl, hydrocarbyl or mixtures thereof, and q is about 1 to about 1000; the diglycidyl ether of a bisphenol is the diglycidyl ether of bisphenol A.  
     
   
   
       12 . The process according to  claim 4  wherein the difunctional amine is ethanolamine or a primary amine having the formula:  
     
       
         
         
             
             
         
       
       wherein R 5  is hydrocarbyl, R 6  is hydrogen, methyl, hydrocarbyl or mixtures thereof, and q is about 1 to about 1000; the diglycidyl ether of a bisphenol is the diglycidyl ether of bisphenol A.  
     
   
   
       13 . The process according to  claim 5  wherein the difunctional amine is ethanolamine or a primary amine having the formula:  
     
       
         
         
             
             
         
       
       wherein R 5  is hydrocarbyl, R 6  is hydrogen, methyl, hydrocarbyl or mixtures thereof, and q is about 1 to about 1000; the diglycidyl ether of a bisphenol is the diglycidyl ether of bisphenol A.  
     
   
   
       14 . The process according to  claim 6  wherein the difunctional amine is ethanolamine or a primary amine having the formula:  
     
       
         
         
             
             
         
       
       wherein R 5  is hydrocarbyl, R 6  is hydrogen, methyl, hydrocarbyl or mixtures thereof, and q is about 1 to about 1000; the diglycidyl ether of a bisphenol is the diglycidyl ether of bisphenol A.