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

Hydroxy-amino-diphosphonates HO-C-n-NH2, with 2 <= n <= 11, have been successfully synthesized via the Kabachnick-Field reaction at 70 degrees C with high yields. These hydroxy compounds are then reacted with methacryloyl chloride to lead to novel amino-diphosphonate methacrylates MAC(n)NP(2) (with 2 <= n <= 11). These highly pure methacrylate monomers were obtained with yields higher than 75%. Radical copolymerizations of MAC(n)NP(2) (with 2 <= n <= 11) with MMA have been conducted and the r(1) values (related to MAC(n)NP(2)) are in the range of 1.1-1.3, and r(2) values (related to MMA) about 0.8; this shows that the diphosphonate groups are statistically bonded to the methacrylic backbone. (C) 2008 Elsevier Ltd. All rights reserved.