Synthesis of a novel methacrylic monomer iniferter and its application in surface photografting on crosslinked polymer substrates

(Methacryloyl ethylenedioxycarbonyl) benzyl N,N-diethyldithiocarbamate (HEMA-E-In) was synthesized and used as a monomer iniferter to develop a novel, photopatternable grafting technology. This molecule functions as both a methacrylic monomer and a photoiniferter (photoinitiator-transfer agent-terminator). The structure of HEMA-E-In was characterized by H-1 NMR, Fourier transform infrared, and ultraviolet-visible spectroscopies. In the presence of the monomer iniferter, methyl methacrylate was polymerized by exposure to 365-nm ultraviolet radiation, confirming the initiation capability of HEMA-E-In. After the copolymerization of HEMA-E-In into a methacrylate-based polymer, attenuated total reflectance Fourier transform infrared spectra revealed that the photoiniferter functionality was present at the surface of this polymeric substrate. Photografting of poly(ethylene glycol) monomethacrylate monomer from the surface caused a significant change in the hydrophobicity of the surface as demonstrated by contact angle measurements. The novel monomer photoiniferter HEMA-E-In initiates the polymerization of bulk monomer and provides a reactive functionality that facilitates further initiation and polymer modification by the polymerization of different monomers. (C). 2002 Wiley Periodicals, Inc.