Novel Quaternary Ammonium Urethane-Dimethacrylates for Copolymers with Low Water Sorption and Solubility

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Abstract
Six novel urethane-dimethacrylates with quaternary ammonium groups (QAUDMAs) were successfully synthesized from 2-(methacryloyloxy)ethyl-2-hydroxyethylmethylalkylammonium bromide (QAHAMA-n, where n was 8 and 10) and diisocyanate (isophorone diisocyanate (IPDI), 4,4′-methylenedicyclohexyl diisocyanate (CHMDI), and 4,4′-diphenylmethane diisocyanate (MDI)). Their chemical structures were confirmed through nuclear magnetic resonance spectroscopy (NMR) and Fourier transform infrared spectroscopy (FTIR). The refractive index (RI) and density (dm) were also determined. The novel QAUDMAs were compounded with common dental dimethacrylates and subsequently photopolymerized. The resulting copolymers, comprising QAUDMA 40 wt.%, bisphenol A glycerolate dimethacrylate (Bis-GMA) 40 wt.%, and triethylene glycol dimethacrylate (TEGDMA) 20 wt.%, were tested for water sorption (WS) and solubility (SL). The WS and SL values decreased following these orderings based on the diisocyanate: IPDI > CHMDI > MDI for WS, and MDI > CHMDI > IPDI for SL. The WS values ranged from 11.50 to 13.82 µg/mm3, and were significantly lower than the recommended maximum for dental materials, 40 µg/mm3. The SL values that met the recommended maximum, 7.5 µg/mm3, ranged from 2.67 to 6.75 µg/mm3. Only the copolymer having the QAHAMA-8- and MDI-derived QAUDMA had the SL slightly exceeding 7.5 µg/mm3, at 7.89 µg/mm3.
Funding Information
  • Silesian University of Technology (04/040/BKM24/0286)

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