Synthesis and characterization of a methacrylate monomer with a thiohydantoin structure
| Autor: | Katsunori Kojima, Akihisa Kodaira, Hiroyasu Koizumi, Hideo Matsumura, Mio Shigeru, Takashi Yamamoto |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Silica gel
Ethyl acetate 030206 dentistry Methacrylate Solvent 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine Monomer Thiohydantoins chemistry Acetone Methacrylates Methyl methacrylate General Dentistry 030217 neurology & neurosurgery Tetrahydrofuran Nuclear chemistry |
| Zdroj: | Journal of Oral Science. 62:256-258 |
| ISSN: | 1880-4926 1343-4934 |
| DOI: | 10.2334/josnusd.19-0005 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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