Low Modulus Fluorosiloxane-Based Hydrogels for Contact Lens Application

Novel methacrylate functionalized fluorinated-siloxy silanes were evaluated for potential use in hydrogels for extended wear contact lens application: methacryloyloxypropyl-tris(3-(2,2,3,3,4,4,5,5-octafluoropentoxy)propyldimethylsiloxy)silane (Tris(F)), methacryloyloxypropyldi(3-(2,2,3,3,4,4,5,5-octafluoropentoxy)propyldimethylsiloxy)methyl-silane (Di(F)), and 1-(methacryloyloxypropyl)-3-(3-(2,2,3,3,4,4,5,5-octafluoropentoxy)propyl)tetra-methyldisiloxane (Mono(F)). The methacrylate fluorinated-silanes were synthesized by the hydrosilation reaction of methacrylate capped hydrido-siloxy silanes with allyloxyoctafluoropentane. An alternate synthetic procedure for Mono(F) was developed. Radical bulk polymerization of the methacrylate functionalized fluorinated-siloxy silanes with hydrophilic monomers, such as dimethylacrylamide, resulted in transparent hydrogels possessing a wide range of water contents, high oxygen permeability, and a low modulus of elasticity.