Poly(oligoethylene glycol methacrylate) hydrogel compositions, and methods of use thereof

Abstract

The present application relates to hydrogel compositions comprising first and second precursor polymers, wherein the precursor polymers are modified poly(oligoethylene glycol methacrylate) copolymers that are crosslinked through electrophile-nucleophile reactions.

1 . A nucleophile-functionalized poly(oligoethylene glycol methacrylate) polymer which comprises a nucleophilic moiety which is a hydrazide or amine derivative, a carbonyl hydrate, an alcohol, cyanohydrin or cyanohydrin derivative, a thiol or thiol derivative, or a phosphorus ylide or derivatives thereof. 
     
     
         2 . The polymer of  claim 1 , wherein the nucleophilic moiety is a hydrazide moiety. 
     
     
         3 . The polymer of  claim 1 , wherein the polymer comprises monomeric units of:
 a. a first monomer which is oligoethylene glycol methacrylate, or a derivative thereof; and   b. at least a second polymerizable monomer which is functionalized or is capable of being functionalized with a hydrazide moiety.   
     
     
         4 . The polymer of  claim 3 , wherein the first monomer has the structure of the formula (I) 
       
         
           
           
               
               
           
         
         R 1  is H, (C 1 -C 10 )alkyl or (C 2 -C 10 )alkynyl; 
         R 2  is H, (C 1 -C 10 )alkyl, (C 2 -C 10 )alkynyl, -(C 0 -C 4 )-alkylene-(C 6 -C 10 )aryl, -(C 0 -C 4 )-alkylene-(C 5 -C 10 )heteroaryl, —C(O)NR′ or —C(O)OR′, wherein R′ is H or (C 1 -C 6 )alkyl, and 
         n is any integer between 6 and 30. 
       
     
     
         5 . The hydrogel composition of  claim 4 , wherein
 R 1  is H or (C 1 -C 4 )alkyl, and   R 2  is H, (C 1 -C 4 )alkyl, -(C 0 -C 2 )-alkylene-phenyl, or —C(O)O—R′, wherein R′ is H or (C 1 -C 4 )alkyl.   
     
     
         6 . The polymer of  claim 3 , wherein the second polymerizable monomer has a carboxylic acid moiety. 
     
     
         7 . The polymer of  claim 6 , wherein the second polymerizable monomer is acrylic acid or a derivative thereof, methacrylic acid, itaconic acid, fumaric acid, maleic acid, or vinylacetic acid. 
     
     
         8 . The polymer of  claim 3 , further comprising one or more monomers which are methacrylic acid, itaconic acid, fumaric acid, maleic acid, vinylacetic acid or tert-butyl-2-acryloylhydrazinecarboxylate (BAHC), 2-dimethylaminoethylmethacrylate (DMAEMA), 2-dimethylaminoethyacrylate (DMAEA), aminoethyl methacrylate (AEMA), allylamine, or derivatives of any of the above, or which has the structure of the formula (II) 
       
         
           
           
               
               
           
         
         wherein 
         R 1  and R 2  are as defined in  claim 4 , and 
         m is any integer between 2-5. 
       
     
     
         9 . A method for coating a porous substrate, the method comprising adsorbing or reacting a compound with the porous substrate, wherein the compound comprises a nucleophile-functionalized poly(oligoethylene glycol methacrylate) polymer as defined in  claim 1 . 
     
     
         10 . The method of  claim 9  wherein the compound comprises a nucleophilic moiety which is a hydrazide or amine derivative, carbonyl hydrate, an alcohol, cyanohydrin or cyanohydrin derivative, a thiol or thiol derivative, or a phosphorus ylide or derivatives thereof. 
     
     
         11 . The method of  claim 10 , wherein the nucleophilic moiety is a hydrazide or amine, or derivative thereof. 
     
     
         12 . The method of  claim 11 , wherein the nucleophilic moiety is a hydrazide or hydrazide derivative. 
     
     
         13 . The method of  claim 9 , wherein the porous substrate is a membrane or filter. 
     
     
         14 . The method of  claim 9 , wherein the porous substrate comprises cellulose. 
     
     
         15 . The method of  claim 9 , further comprising reacting the compound with an electrophile-functionalized poly(oligoethylene glycol methacrylate) second polymer, wherein the compound and second polymer are crosslinked through covalent bonds by reaction of the nucleophilic and electrophilic moieties. 
     
     
         16 . The method of  claim 15 , wherein a hydrogel is formed on the substrate. 
     
     
         17 . A coated porous substrate comprising a porous substrate and a compound adsorbed or reacted with the porous substrate, wherein the compound comprises a nucleophile-functionalized poly(oligoethylene glycol methacrylate) polymer as defined in  claim 1 . 
     
     
         18 . The coated porous substrate of  claim 17 , wherein the compound comprises a nucleophilic moiety which is a hydrazide or amine derivative, carbonyl hydrate, an alcohol, cyanohydrin or cyanohydrin derivative, a thiol or thiol derivative, or a phosphorus ylide or derivatives thereof. 
     
     
         19 . The coated porous substrate of  claim 18  wherein the compound is a hydrazide or amine derivative. 
     
     
         20 . The coated porous substrate of  claim 17 , wherein the porous substrate is a membrane or filter