New perfluoroalkylated amphiphilic methacrylates bearing sulfinyl group as monomers for biomedical applications: water content and oxygen permeability of their copolymers with DEGMA

Perfluoroalkylated methacrylates 7a–c bearing sulfinyl group within a straight-chain ester group, i.e. CH2=C(CH3)CO2CH2CH2S(O)–CH2CH2CF2(CF2CF2)nCF3 (n = 1–3) were prepared by two alternative synthetic sequences from 2-[(polyfluoroalkyl)sulfanyl]ethanols HOCH2CH2SCH2CH2CF2(CF2CF2)nCF3 (n = 1–3) in overall yields of 88–91%. Copolymers of 7a–c with diethylene glycol methacrylate (DEGMA) prepared in bulk under radical conditions display high transparency, increased water content and good oxygen permeability properties, which are advantageous for their application in ophthalmology and as prosthetic materials.

Graphical abstractProperties of hydrogels: transparency, water content 7.5–49.4%, oxygen permeability 10–31 barrer.Figure optionsDownload full-size imageDownload as PowerPoint slide