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Methacrylate‐capped fluoro side chain siloxanes: Synthesis, characterization, and their use in the design of oxygen‐permeable hydrogels
Author(s) -
Künzler J.,
Ozark R.
Publication year - 1997
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/(sici)1097-4628(19970808)65:6<1081::aid-app3>3.0.co;2-g
Subject(s) - polymer chemistry , methacrylate , hydrosilylation , self healing hydrogels , monomer , octamethylcyclotetrasiloxane , siloxane , side chain , oxygen permeability , radical polymerization , polymerization , chemistry , materials science , polymer , organic chemistry , catalysis , oxygen
Methacrylate end‐capped 3‐(2,2,3,3,‐tetrafluoropropoxy)propyl, 3‐(2,2,3,3,4,4,5,5‐octafluoropentoxy)propyl, and 3‐(2,2,3,3,4,4,5,5,6,6,7,7‐dodecafluorotridecoxy)propyl side chain siloxanes were evaluated for potential use in hydrogels for contact lens application. The preparation of the methacrylate end‐capped perfluoro side chain siloxanes was accomplished in two relatively simple synthetic steps. The first step consisted of the acid‐catalyzed co‐ring opening polymerization of octamethylcyclotetrasiloxane, tetramethylcyclotetrasiloxane, and 1,3‐ bis ‐methacryloxybutyltetramethyldisiloxane, followed by a platinum‐catalyzed hydrosilation with the tetrafluoro‐, octafluoro‐, and dodecafluoro‐substituted allylic ethers. The incorporation of the terminal [—CF 2 —H] functionality had a dramatic effect on the increased solubility of the fluoro siloxane with hydrophilic monomers. Radical bulk polymerization of the methacrylate‐capped fluoro side chain siloxanes with hydrophilic monomers, such as dimethylacrylamide and N ‐vinyl pyrrolidinone, resulted in transparent hydrogels possessing a wide range of water contents, high oxygen permeability, and a low modulus of elasticity. © 1997 John Wiley & Sons, Inc. J Appl Polym Sci 65:1081–1089, 1997