An efficient process for synthesizing and hydrolyzing a phosphonated methacrylate: Investigation of the adhesive and anticorrosive properties

A new phosphonated methacrylate, namely dimethyl(methacryloyloxy)methyl phosphonate (MAPC(1)), has been synthesized using paraformaldehyde and potassium carbonate according to the Pudovik reaction. The quantitative synthesis of MAPC(1) was followed by selective hydrolysis of the ester group with sodium bromide to replace NaI (imparting non-negligible ecological impact). Pure MAPC(1)(OH) was obtained in high yield and efficiently copolymerized with MMA. The r(1) for MAPC(1)(OH) and r(2) (for MMA) values are 0.99 and 1.02, respectively, which indicates that the monophosphonic groups are statistically linked to the methacrylate backbone. When blended with PVDF, MMA/MAPC(1)(OH) copolymers show very good adhesion promoters in both dry and wet conditions and subsequently provide good anticorrosive properties. (C) 2008 Wiley Periodicals, Inc.