Investigation on radical polymerization of 2-methylene-1,3-dioxolanes and 2-methylene-1,3-oxazolidines

✍ Scribed by Th. Schulze; J. Letsch; E. Klemm

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 501 KB
• Volume: 34
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(19960115)34:1<81::aid-pola8>3.0.co;2-6

✦ Synopsis

The reaction of 2-methylene-l,3-dioxolanes and 2-methylene-1,3-oxazolidines with benzoyl peroxide (acceptor radical) and with N-ethylmaleimide (acceptor) was investigated. It was shown that benzoyl peroxide adds to monomers la and lb, giving the corresponding linear diester amides la and lb respectively. The oxazolidine lc adds benzoyl peroxide, without ring opening, by addition to the exomethylene group. Together with N-ethylmaleimide the oxazolidines la or lb produce deep-colored charge transfer complexes, resulting in high molecular poly-N-ethylmaleimides probably via a radical mechanism. The 1,3-dioxolanes 2a and 2b were radically polymerized to produce polyacetals by vinyl polymerization. 2c was polymerized to produce randomly containing acetal units and ester units. The mechanism of polymerization of 2e is complex, affording polymers of nonuniform character. 2-Methylene-4-phenyl-1,3-dioxolane polymerization leads to polyester as the main structure, and to a lesser degree polyacetal structures. The chemical structures of the polymers were confirmed by NMR spectra and elemental analysis.