Synthesis and structural characterization of novel urethane-dimethacrylate monomer with two quaternary ammonium groups

Introduction: Consumption of sugar rises worldwide every year resulting in increasing dental health issues, such as dental caries. Dental caries arise from sugar metabolism, which is carried out by pathogenic bacteria living in a human's mouth, and insufficient dental hygiene. The WHO report from 2022 states that 2 billion adult people and 514 million children are stricken by caries of teeth. In dental caries treatment, contaminated tissue must be removed and the resulting cavity is usually filled with a composite material having a dimethacrylate matrix. Commercially available dimethacrylate monomers give dental materials proper physicochemical properties and support their mechanical properties. However, they do not provide antibacterial activity. This problem can be solved by the application of monomers with quaternary ammonium (QA) groups. The positively charged QA group interacts with the negatively charged surface of bacteria cells, which leads to bacteria death. Current research concerning monomers with QA groups shows that they are effective against bacteria, however, do not ensure optimum performance characteristics of composite dental materials.

Aim of the research: Achievement of a novel urethane-dimethacrylate monomer with two QA groups (QAUDMA) for possible application in dentistry.

Results: QAUDMA was synthesized from 2-(methacryloyloxy)ethyl-2-decylhydroxyethylmethylammonium bromide and commercial diisocyanate.

Aim of presentation: Presentation of the chemical structure of novel QAUDMA, and its synthesis route, supported with detailed 1H and 13C NMR and FTIR analyses.