Synthesis and characterization of a methacrylate monomer with a thiohydantoin structure

The purpose of the current study was to synthesize a methacrylate monomer with a thiohydantoin structure. In a flask, (2-thiohydantoin-4-yl) propionic acid, 10-hyroxydecyl methacrylate, 4-dimethylaminopyridine, and tetrahydrofuran (THF) were placed in a nitrogen atmosphere. A THF solution of N,N'-dicyclohexylcarbodiimide was added and stirred at room temperature. Ethyl acetate and n-hexane were then added to the reaction mixture. The reacted slurry was purified by chromatography with silica gel and hexane-ethyl acetate gradient elution solvent. The structure of the compound was assigned with proton nuclear magnetic resonance spectrum analysis, infrared spectroscopy, and high-resolution mass spectral analysis. The colorless viscous liquid obtained in yield of 49% was characterized as 10-methacryloyloxydecyl-(2-thiohydantoin-4-yl)propionate (MDTHP) or 10-((3-(5-oxo-2-thioxysoimidazolidin-4-yl)propanoyl)oxy)decyl methacrylate (2-THPDM). The MDTHP was soluble to acetone, isopropanol, and methyl methacrylate up to 2.6% or more. This compound could be potentially applicable as a functional monomer for bonding metals and alloys.