Synthesis, Antibacterial Activity and Hydrolytic Resistance of (Meth)acrylamide-based Monomers for Dental Resin Adhesive

IF 4.1 2区 化学 Q2 POLYMER SCIENCE
Prompat Promphet, Supattra Kaewtaro, Supitcha Talungchit, Somjin Ratanasathien, Piangkwan Saiprasert, Nattawut Decha, Chittreeya Tansakul
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引用次数: 0

Abstract

Dental resin adhesive is a mixture of monomers used as an adhesive in resin-based composite tooth restoration. Methacrylate monomers used in these adhesives are susceptible to hydrolysis by bacterial enzymes, leading to limitation of their lifespan. To overcome this issue, in this research series of quaternary ammonium-containing methacrylamides, MDAB (methacrylamidoethyl dimethyl ammonium bromide) and MDAF (methacrylamidoethyl dimethyl ammonium fluoride), acrylamides, ADAB (acrylamidoethyl dimethyl ammonium bromide) and bismethacrylamides, bis-MMAI (bis(2-methacrylamidoethyl)methyl ammonium iodide) were synthesized. These new monomers exhibited antibacterial properties against common bacteria found in tooth cavities, which are S. mutans and E. faecalis. Extra methyl moiety on polymerizable group and long alkyl chain length increased antibacterial properties as well as cytotoxicity against MDPC.23 mouse dental papilla cell lines. Acrylamides, ADAB showed the least cytotoxicity with higher MBC values than the commonly used methacrylate monomer, bis-GMA and the only antibacterial methacrylate-based monomer currently used in commercial resin adhesives, MDPB (methacryloyldodecylpyridinium bromide). Steric hindrance and lipophilicity of bismethacrylamides in bis-MMAI series reduced antibacterial activities and also significantly enhanced cytotoxicity of the monomers. Moreover, bromide and fluoride counter ions in MDAB and MDAF, respectively, did not cause any difference in antibacterial effects. Additionally, all synthesized (meth)acrylamide monomers demonstrated greater stability against hydrolysis under acidic conditions compared to the methacrylate MDPB. Degree of conversions of synthesized monomers were lower than that of MDPB at the beginning of polymerization due to the higher viscosity, but were comparable at the latter stage. Methyl group on methacrylamides in MDAB and the highest viscosity of bismethacrylamides, bis-MMAI reduced degree of conversions of the monomers. TADAB (tetradecylacrylamidoethyl dimethyl ammonium bromide) incorporated in resin adhesive reduced water solubility of the cured resin under acidic condition.

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来源期刊
Polymer
Polymer 化学-高分子科学
CiteScore
7.90
自引率
8.70%
发文量
959
审稿时长
32 days
期刊介绍: Polymer is an interdisciplinary journal dedicated to publishing innovative and significant advances in Polymer Physics, Chemistry and Technology. We welcome submissions on polymer hybrids, nanocomposites, characterisation and self-assembly. Polymer also publishes work on the technological application of polymers in energy and optoelectronics. The main scope is covered but not limited to the following core areas: Polymer Materials Nanocomposites and hybrid nanomaterials Polymer blends, films, fibres, networks and porous materials Physical Characterization Characterisation, modelling and simulation* of molecular and materials properties in bulk, solution, and thin films Polymer Engineering Advanced multiscale processing methods Polymer Synthesis, Modification and Self-assembly Including designer polymer architectures, mechanisms and kinetics, and supramolecular polymerization Technological Applications Polymers for energy generation and storage Polymer membranes for separation technology Polymers for opto- and microelectronics.
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