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Polymers 2018, 10(7), 711; https://doi.org/10.3390/polym10070711

Synthesis and Aqueous Solution Properties of an Amino Bisphosphonate Methacrylate Homopolymer via RAFT Polymerization

Institut Charles Gerhardt—UMR-CNRS 5253, Ingénierie et Architectures Macromoléculaires, ENSCM, 8 rue de l’Ecole normale, CEDEX 5, 34296 Montpellier, France
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Received: 30 May 2018 / Revised: 21 June 2018 / Accepted: 22 June 2018 / Published: 27 June 2018
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Abstract

The present contribution reports on the synthesis via reversible addition-fragmentation chain transfer (RAFT) polymerization of a methacrylate derivative bearing an aminobisphosponate moiety as a pendant group, namely, ethyl N,N-tetramethylbis(phosphonate)-bis(methylene) amine methacrylate (MAC2NP2). The polymerization was performed by the use of cyanoisopropyl dithiobenzoate as chain transfer agent at 70 °C in various solvents with different polarities including N,N-dimethylformamide, acetonitrile, tetrahydrofuran, and in bulk. Best results were obtained in N,N-dimethylformamide where higher conversions and polymerization rates were noticed. The successful hydrolysis of the phosphonate ester groups was performed using bromotrimethylsilane with excellent yields leading to the formation of highly water soluble and pH-responsive polymers. Finally, a preliminary solution behavior study was carried out by investigating the aqueous solution properties of synthesized amino bisphosphonate methacrylate homopolymers and their phosphonic acid analogs via potentiometric titration and zeta potential measurements. View Full-Text
Keywords: amino bisphosphonate; RAFT polymerization; solvent polarity; hydrolysis; amino bisphosphonic acid; pH-responsive polymers amino bisphosphonate; RAFT polymerization; solvent polarity; hydrolysis; amino bisphosphonic acid; pH-responsive polymers
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Falireas, P.G.; Negrell, C.; David, G. Synthesis and Aqueous Solution Properties of an Amino Bisphosphonate Methacrylate Homopolymer via RAFT Polymerization. Polymers 2018, 10, 711.

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