Poly(N-isopropylacrylamide-co-2-((diethylamino)methyl)-4-formyl-6-methoxyphenyl acrylate) Environmental Functional Copolymers: Synthesis, Characterizations, and Grafting with Amino Acids

Vanillin was used to synthesize a new derivative with an active aldehyde group and response to pH. It is named 2-((diethylamino) methyl)-4-formyl-6-methoxyphenyl acrylate, abbreviated to DEAMVA. The chemical structures were evaluated by ¹H, ¹³C nuclear magnetic resonance (NMR), infrared (IR), and UV-Vis-spectroscopy, and all results demonstrated good statement. In order to achieve the dual responsive behavior thermo-pH with functionality, free radical polymerization of N-isopropylacrylamide with DEAMVA in different molar ratios (5, 10, 15 mol%) has been used, with azobisisobutyronitrile (AIBN) as the initiator. The chemical structure of the polymers was investigated by ¹H NMR and IR. The dual responsive functional copolymer was exposed to a grafted process with tryptophan and tyrosine, both of which were also evaluated by ¹HNMR and IR. Copolymers before and after grafting were physically investigated by size exclusion chromatography (SEC) for estimation of the molecular weight, the glass transition temperature by differential scanning calorimeter (DSC) and scanning electron microscope (SEM) for the surface morphology. The phase separation or lower critical solution temperature (LCST) (T_c) of the polymer solution was determined not only by a turbidity method using the change in the transmittance with temperature, but also by micro-DSC. The conversion to an amino acid-grafted polymer was detected through Beer’s law for the absorption of the ⁻CH=N- imine group by UV-Vis-Spectroscopy.