New N,N-amino-diphosphonate-containing methacrylic derivatives, their syntheses and radical copolymerizations with MMA

Hydroxy-amino-diphosphonates HO–Cn–NH2, with 2 ⩽ n ⩽ 11, have been successfully synthesized via the Kabachnick-Field reaction at 70 °C with high yields. These hydroxy compounds are then reacted with methacryloyl chloride to lead to novel amino-diphosphonate methacrylates MACnNP2 (with 2 ⩽ n ⩽ 11). These highly pure methacrylate monomers were obtained with yields higher than 75%. Radical copolymerizations of MACnNP2 (with 2 ⩽ n ⩽ 11) with MMA have been conducted and the r1 values (related to MACnNP2) are in the range of 1.1–1.3, and r2 values (related to MMA) about 0.8; this shows that the diphosphonate groups are statistically bonded to the methacrylic backbone.