Synthesis of novel copolymers obtained from acceptor/donor radical copolymerization of phosphonated allyl monomers and maleic anhydride

• Published in: Journal of polymer science. Part A, Polymer chemistry Polymer chemistry, 2011-09, Vol.49 (18), p.3905-3910
• Main Authors: Negrell-Guirao, C., David, G., Boutevin, B., Chougrani, K.
• Format: Article
• Language: English
• Subjects: AD copolymerization; allyl monomer; Applied sciences; Chemical Sciences; Conversion; Copolymerization; Copolymers; dioxaphosphorinane; Exact sciences and technology; flame retardance; heteroatom-containing polymers; kinetics (polym.); Maleic anhydride; Monomers; Organic polymers; Phosphonates; Physicochemistry of polymers; Polymers; Preparation, kinetics, thermodynamics, mechanism and catalysts; radical polymerization; Radicals; Residues; thermogravimetric analysis
• ISSN: 0887-624X; 1099-0518; 0449-296X; 1099-0518; 1542-9350
• DOI: 10.1002/pola.24827

A series of four phosphonated‐bearing allyl monomers, that is, diethyl‐1‐allylphosphonate (AP), dimethyl‐1‐allyloxymethylphosphonate (AOP), 5‐ethyl‐5‐(allyloxymethyl)‐2‐oxo‐1,3,2‐dioxaphosphorinane (AEDPH), and 2‐benzyl‐5‐ethyl‐5‐(allyloxymethyl)‐2‐oxo‐1,3,2‐dioxaphosphorinane (AEDPBn) were synthesized. These monomers were then copolymerized by free radical polymerization in the presence of maleic anhydride, thus leading to alternated copolymers with phosphonate moieties. It was shown that both monomer conversion and reaction rate were dependent on the phosphonate moieties carried out by the allyl monomer: the bulkier the phosphonate group, the higher the polymerization rate. Thermogravimetric analysis of the copolymers revealed a high content of residue, also varying with the nature of the phosphonate moieties. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011 Free radical copolymerization of maleic anhydride was successfully carried out in the presence of allyl monomers carrying phosphonate moieties, i.e.that is, diethyl phosphonate or dioxaphosphorinane group. Both monomer conversion and reaction rate were dependent on the phosphonate moieties carried out by the allyl monomer: the bulkier the phosphonate group, the higher the polymerization rate. Thermogravimetric analysis of the copolymers revealed a high content of residue, also varying with the nature of the phosphonate moieties.