Highly reactive, liquid diacrylamides via synergistic combination of spatially arranged curing moieties

Six polymerizable N,N’-diacylamides containing spatially arranged N-acryl, N-allyl and/or N-alkyl groups were prepared via two-step syntheses and characterized by (1)H/(13)C NMR-spectra, refractive index (RI) and viscosity measurements. Photo DSC measurements on activated samples provided reactivity parameters ∆H(p), R(p,max) and t(max), while FTIR spectra before and after curing elucidated the underlying polymerization mechanism. Mechanical testing of the obtained polymers exhibited gradual differences in network densities, depending on the intramolecular arrangement and number of functional groups. Overall, a general building principle for highly reactive, liquid diacrylamides via synergistic combination of optimally arranged functional groups could be identified. The highest possible level of intramolecular synergism was found for low viscous N,N'-diacryloyl-N,N'-diallyl-1,4-but-2-enediamine.