Method of Making Silicone Hydrogels with Fluorinated Side Chain Polysiloxanes

Abstract

A method of making a silicone hydrogel contact lens from a monomer mixture that includes: N-vinyl-N-methyl acetamide, N-vinyl pyrrolidone or a mixture thereof; a monofunctional polysiloxanylalkyl monomer, and a polysiloxane-containing monomer having a perfluorinated side chain on a terminal carbon. The monomer mixture is charged to a mold and then subjected to spin casting or static casting. The casted mold is exposed to visible light or UV radiation. The resulting silicone hydrogel contact lens has an oxygen permeability of at least about 120 Barrers, a water content of at least about 20 weight percent, and a modulus from 40 g/mm 2 to 97 g/mm 2 .

1 . A method of making a silicone hydrogel contact lens from a monomer mixture, the method comprising:
 preparing a monomer mixture that includes: N-vinyl-N-methyl acetamide, N-vinyl pyrrolidone or a mixture thereof; a monofunctional polysiloxanylalkyl monomer, and a polysiloxane-containing monomer having a perfluorinated side chain on a terminal carbon;   charging the prepared monomer mixture to a mold and subjecting the charged mold to spin casting or static casting; and   exposing the casted mold to visible light or UV radiation;   wherein said silicone hydrogel has an oxygen permeability of at least about 120 Barrers, a water content of at least about 20 weight percent, and a modulus from 40 g/mm 2  to 97 g/mm 2 .   
     
     
         2 . The method of  claim 1  wherein the charged mold is subject to spin casting and visible light. 
     
     
         3 . The method of  claim 1  wherein the charged mold is subject to static casting and visible light. 
     
     
         4 . The method of  claim 1  wherein the charged mold is subject to spin casting and UV radiation. 
     
     
         5 . The method of  claim 1  wherein the charged mold is subject to static casting and UV radiation. 
     
     
         6 . The method of  claim 1  wherein the silicone hydrogel contact lens has a modulus from 61 g/mm 2  to 97 g/mm 2 . 
     
     
         7 . The method of  claim 1  wherein the silicone hydrogel contact lens has a modulus from 70 g/mm 2  to 92 g/mm 2 . 
     
     
         8 . The method of  claim 1  wherein the monofunctional polysiloxanylalkyl monomer is selected from the group consisting of 3-[tris(trimethylsiloxy)silyl]propyl vinylcarbamate and 3-[tris(trimethylsiloxy)silyl]propyl vinylcarbonate. 
     
     
         9 . The method of claim  18  having an oxygen permeability from 120.9 Barrers to 133.6 Barrers. 
     
     
         10 . The method of  claim 1  wherein the polysiloxane-containing monomer having a perfluorinated side chain is present in the monomer mixture from 25% to 41% by weight of total monomer in the monomer mixture.