Acrylamide Based Monomers Effectively Replace Acrylate Based Monomers in Hydrogel Synthesis
Faculty Mentor Information
Dr. Matthew Bernards, University of Idaho
Presentation Date
7-15-2026
Abstract
Hydrogels have many applications in drug delivery, wound healing, and tissue replacement technologies. Novel hydrogels under development have two key properties setting them apart depending on the application. State-of-the-art hydrogels are resistant to nonspecific protein adhesion (non-fouling). They also have tunable weight percent degradation. Hydrogels formed from the monomers 2-carboxy ethylacrylate (CAA) and [2-(acryloyloxy)ethyl]trimethylammonium (TMA) were previously demonstrated to be non-fouling, but they degraded under acidic conditions over 60 days. Acrylamide based monomers 3-acryalmidopropanoic acid (APA) and N,N,N-trimethyl-3-acrylamidopropanamine iodide (TAP) are proposed as alternatives to improve resistance to weight percent degradation. Because these monomers cannot be commonly obtained through commercial distributers, they must be synthesized. APA was synthesized by reacting beta-alanine with acrylic anhydride. APA was also synthesized with an alternative approach by reacting 3-bromoproanoic acid with acrylamide. TAP was synthesized by reacting N,N-dimethylethylenediamine with acrylic anhydride, followed by methyl iodide. APA purification efforts are ongoing, while TAP was effectively purified after synthesis. Further TAP was mixed with CAA to successfully form a hydrogel using photoinitiated polymerization. APA will be tested in a similar way upon its purification and long term degradation studies are underway.
Acrylamide Based Monomers Effectively Replace Acrylate Based Monomers in Hydrogel Synthesis
Hydrogels have many applications in drug delivery, wound healing, and tissue replacement technologies. Novel hydrogels under development have two key properties setting them apart depending on the application. State-of-the-art hydrogels are resistant to nonspecific protein adhesion (non-fouling). They also have tunable weight percent degradation. Hydrogels formed from the monomers 2-carboxy ethylacrylate (CAA) and [2-(acryloyloxy)ethyl]trimethylammonium (TMA) were previously demonstrated to be non-fouling, but they degraded under acidic conditions over 60 days. Acrylamide based monomers 3-acryalmidopropanoic acid (APA) and N,N,N-trimethyl-3-acrylamidopropanamine iodide (TAP) are proposed as alternatives to improve resistance to weight percent degradation. Because these monomers cannot be commonly obtained through commercial distributers, they must be synthesized. APA was synthesized by reacting beta-alanine with acrylic anhydride. APA was also synthesized with an alternative approach by reacting 3-bromoproanoic acid with acrylamide. TAP was synthesized by reacting N,N-dimethylethylenediamine with acrylic anhydride, followed by methyl iodide. APA purification efforts are ongoing, while TAP was effectively purified after synthesis. Further TAP was mixed with CAA to successfully form a hydrogel using photoinitiated polymerization. APA will be tested in a similar way upon its purification and long term degradation studies are underway.