Abstract
The synthesis of new functional monomers based on vanillin is reported. The monomers further were used in the synthesis of different temperature-responsive photo cross-linkable polymers via free radical polymerization with N-isopropyl acrylamide and a maleimide photo cross-linker. These polymers were characterized by NMR, FTIR and UV spectroscopy, as well as gel permeation chromatography (GPC) and differential scanning calorimetry (DSC). Critical solution temperatures were determined by UV spectroscopy. Hydrogel thin films were formed by spin coating of a polymer solution over gold with adhesion promotor followed by cross-linking by UV irradiation. The swelling properties were determined by surface plasmon resonance coupled with optical waveguide spectroscopy. The swelling behavior of the hydrogel films was determined as a function of temperature. The incorporation of a dialkyl amino group compensated the hydrophobic effect of the vanillin monomer. Transition temperatures in the physiological range could be obtained.
Highlights
Smart polymers or stimuli-responsive polymers have been widely used due to their practical interests, and several types of responsiveness, including temperature, pH, light, pressure, magnetic and electrical fields, have been reported [1]
The first step was the reaction of vanillin with diethylamine for DEAMVA or dimethylamine for DMAMVA and formaldehyde according to a Mannich reaction mechanism
New monomers based on vanillin were copolymerized with N-isopropyl acrylamide (NIPAAm) and DMIA
Summary
Smart polymers or stimuli-responsive polymers have been widely used due to their practical interests, and several types of responsiveness, including temperature, pH, light, pressure, magnetic and electrical fields, have been reported [1]. These kinds of materials were known in nature in some examples, like the leaves of Mimosa pudica and Venus flytrap [2]. These polymers and hydrogels are responsive towards more than one stimulus, but the majority of studies have focused on pH and temperature variation [1,3,4,5,6,7]. The utilization of the reactive aldehyde group will be reported in a future work
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