Preparation of Amino-Functionalized Poly(N-isopropylacrylamide)-Based Microgel Particles

Abstract

Responsive cationic microgels are a promising building block in several diagnostic and therapeutic applications, like transfection and RNA or enzyme packaging. Although the direct synthesis of cationic poly(N-isopropylacrylamide) (PNIPAm) microgel particles has a long history, these procedures typically resulted in low yield, low incorporation of the cationic comonomer, increased polydispersity, and pure size control. In this study, we investigated the possibility of the post-polymerization modification of P(NIPAm-co-acrylic acid) microgels to prepare primary amine functionalized microgels. To achieve this goal, we used 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride (EDC) mediated coupling of a diamine to the carboxyl groups. We found that by controlling the EDC excess in the reaction mixture, the amine functionalization of the carboxyl functionalized microgel could be varied and as much as 6–7 mol% amine content could be incorporated into the microgels. Importantly, the reaction was conducted at room temperature in an aqueous medium and it was found to be time efficient, making it a practical and convenient approach for synthesizing primary amine functionalized PNIPAm microgel particles.