Synthesis of poly(N, N-dimethylcarbamoylmethylene) as a polymer homolog of N, N-dimethylacetamide

SummaryA novel polymer homolog of N,N-dimethylacetamide (DMAc) having amide groups on all main chain carbons, poly(N,N-dimethylcarbamoylmethylene) 1, was prepared by heating poly(di-t-butyl fumarate) 2 at 180 °C for 2 hours followed by treatment with hexamethylphosphoramide at 180 °C for 5 hours. The structure of the obtained polymer 1 was confirmed by 1H-, 13C-NMR and IR spectroscopy. The polymer 1 actually showed the properties based on its repeating structures. 1 had the amphiphilicity and was soluble both in protic and aprotic solvents. Furthermore, 1 showed the miscibility with commodity polymers such as poly(N-vinylpyrrolidone), poly(vinyl alcohol) and poly(vinyl chloride). In comparison with another polymer homolog of DMAc, poly(2-methyl-2-oxazoline), the polymer 1 exhibited better miscibility with poly(N-vinylpyrrolidone).