Dual-phase zwitterionic monomers

Abstract

Hydrogel materials used in the manufacture of biocompatible medical devices, for example, hydrogel materials having desirable physical properties for use as a contact lens. A composition contains at least one vinyl containing monomer, a methacrylate(acrylate) monomer, methacrylate (acrylate) prepolymers, crosslinking agents and monomers having the structure as shown in Formula 1:where R1 is a vinyl functionality capable of radical polymerization with specific preference for N-vinyl lactam derivatives and R2 is a zwitterionic functionality. The materials utilize a two-phase polymerization strategy.

What is claimed is: 
     
         1 . A composition comprising a monomer having the structure as shown in Formula 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1  is selected from the group as shown below in formulas (II)-(VIII): 
 
       
         
           
           
               
               
           
         
         wherein Y 1  and Y 2  are independent of one other and each on of Y1 and Y2 is a linkage selected from the group consisting of a direct bond, C 1 -C 6  divalent radical, O, NW, C(O), C(O)NR a , NR a C(O), OC(O)NH, NHC(O)O, NR a C(O)NH, NHC(O)NR a , C(O)O, OC(O), NHC(O)NHZ 0 —NH—C(O)NH, OC(O)NHZ 0 —NH—C(O)O, OC(O)NHZ 0 —NH—C(O)NH, and NHC(O)NHZ 0 —NH—C(O)O; where R a  is H, C 1 -C 4  alkyl or C 1 -C 3  alkanol, and Z 0  is a linear or branched C 2 -C 12  alkylene divalent radical, or a C 5 -C 7  cycloaliphatic divalent radical; 
         wherein Z 1  is selected from the group consisting of a direct bond, a C 1 -C 12  unsubstituted or substituted, linear or branched alkylene divalent radical, an unsubstituted phenylene divalent radical, a C 5 -C 7  cycloaliphatic divalent radical, and a C 7 -C 12  arylalkylene divalent radical, wherein at least two of the groups Y 1 , Y 2 , Z 1  and Z 2  is not a direct bond, 
         wherein R 2  for formulas II-VII is selected from the group of zwitterionic functionality as shown in the following formulas: 
       
       
         
           
           
               
               
           
         
         where R is selected from the group consisting of a direct bond, C 1 -C 6  divalent radical, O, NR a , C(O), C(O)NR a , NR a C(O), OC(O)NH, NHC(O)O, NR a C(O)NH, NHC(O)NR a , C(O)O, OC(O), NHC(O)NHZ 0 —NH—C(O)NH, OC(O)NHZ 0 —NH—C(O)O, OC(O)NHZ 0 —NH—C(O)NH, and NHC(O)NHZ 0 —NH—C(O)O; where R a  is H, C 1 -C 4  alkyl or C 1 -C 3  alkanol, and Z 0  is a linear or branched C 2 -C 12  alkylene divalent radical, or a C 5 -C 7  cycloaliphatic divalent radical; 
         wherein in the case of the structure VIII, R 2  is selected from the following anionic groups to provide a zwitterionic monomer capable of cyclo-copolymerizing: 
       
       
         
           
           
               
               
           
         
         where R is selected from the group consisting of a direct bond, C 1 -C 6  divalent radical, O, NR a , C(O), C(O)NR a , NR a C(O), OC(O)NH, NHC(O)O, NR a C(O)NH, NHC(O)NR a , C(O)O, OC(O), NHC(O)NHZ 0 —NH—C(O)NH, OC(O)NHZ 0 —NH—C(O)O, OC(O)NHZ 0 —NH—C(O)NH, and NHC(O)NHZ 0 —NH—C(O)O; where R a  is H, C 1 -C 4  alkyl or C 1 -C 3  alkanol, and Z 0  is a linear or branched C 2 -C 12  alkylene divalent radical, or a C 5 -C 7  cycloaliphatic divalent radical. 
       
     
     
         2 . The composition of  claim 1  further comprising at least one vinyl monomer selected from the group consisting of N-vinyl-2-pyrrolidone, N-vinyl piperidone, N-vinyl-caprolactam, N-vinylimidazolidone, N-vinylsuccinimide, N-vinylformamide, N-vinyl urea, N-vinylcarbamate, O-vinyl carbonate and any one mixture thereof. 
     
     
         3 . The composition of  claim 1 , further comprising at least one (meth)acrylic monomer. 
     
     
         4 . The composition of  claim 3 , wherein the (meth)acrylic monomer is 4-t-butyl-2-hydroxycyclohexylmethacrylate or another cycloaliphatic strengthening agents. 
     
     
         5 . The composition of  claim 3 , wherein the(meth)acrylic monomers include functional monomers selected from the group consisting of carboxybetaines, sulfobetaines and phosphobetaines. 
     
     
         6 . The composition of  claim 1  further comprising silicone monomers selected from the group consisting of Tris-(trimethylsiloxy)-3-methacryloxypropyl methacrylate (Tris), 3-methacryloxy-2-hydroxypropyloxy) propylbis(trimethylsiloxy)-methylsilane (Sigma), and other siloxy silane monomers, and mixture thereof, wherein the mixture thereof is present from 8% to 60% by weight of the composition. 
     
     
         7 . The composition of  claim 1  further comprising silicone prepolymers selected from the group consisting of mono or difunctional polydimethyl siloxanes and mixtures thereof present from 8% to 60% by weight of the composition. 
     
     
         8 . The composition of  claim 1 , wherein Z 1  is a branched alkylene divalent radical that includes one or more linkages of O, NR a , and C(O). 
     
     
         9 . The composition of  claim 1 , further comprising a crosslinking agent. 
     
     
         10 . A hydrogel polymer prepared from the composition of  claim 1 . 
     
     
         11 . The hydrogel polymer of  claim 10  with a water content of 30 to 90 wt percent. 
     
     
         12 . A contact lens prepared with the hydrogel polymer according to  claim 10 .