Macromolecules, Vol.36, No.17, 6340-6345, 2003
1,3-dipolar cycloaddition in polymer synthesis. 1. Polyadducts with flexible spacers derived from Bis(N-methylnitrone)s and Bis(N-phenylmaleimide)s
The thermal 1,3-dipolar polycycloaddition of N,N'-dimethyl-p-phenylenedinitrone (3) and 4,4'-hexanediyldioxydi(N-methyl-p-phenylenenitrone) (10) with N,N'-(1,4-phenylene)dimaleimide and 1,6-hexanediylbis(carbamic acid) bis(N-methyl-p-phenylenenitrone) ester (12) with 1,6-hexanediylbis(carbamic acid) bis[N-(p-phenylene)maleimide] ester (16) in DMF solution and nitrogen atmosphere lead to the formation of corresponding polyadducts 5, 13 and 17. The comparison of H-1 NMR, C-13 NMR and IR spectra of a model compound 2-methyl-3-(4'-hydroxyphenyl)isoxazolidine-4,5-dicarboxyphenylimide (8) with model polymer 5 verified that the main chain is bearing an isoxazolidine ring. The molecular weight was found to be in the region of 28900-3600 (M-w) and 6600-1500 g/mol (M-n) according to SEC measurements. It was not possible to determine glass transition temperatures (T-g) for 17 by DSC measurements; for 5 and 13, T. values were found at 67 and 52 degreesC, respectively. Decomposition temperatures (T-d) for polymer samples 5, 13 and 17 were 260, 247, and 192 degreesC, respectively. Polymer 17 exhibits good ability for coating formation on a glass surface.