Synthesis and characterization of a methacrylate monomer with a thiohydantoin structure

Abstract

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. Keywords; adhesive, bonding, noble metal alloy, thiol, thione Solubility of monomersThe solubility of the synthesized monomer in the current project and VBATDT [1] was evaluated. The solvents used were acetone, isopropanol, and MMA. Monomers were separately added to the three solvents and magnetically stirred for 30 min. The resultant transparent solution was judged as a solution within the soluble wt% concentration of each monomer.

Isolation and Identification of Cytotoxic Compounds Present in Biomaterial Life®

“…This study also highlights the utility of chemical techniques for developing and evaluating biomaterials, which have often a complex constitution with dozens of components [ 32 , 33 , 34 ]. Additionally, chemical reactions occur during their manipulation, application, and later when in contact with the living tissues [ 19 , 35 , 36 ].…”

Evaluation of the effects of three pretreatment conditioners and a surface preparation system on the bonding durability of composite resin adhesive to a gold alloy

“…Similarly, the VTD monomer was reported to exhibit high bonding durability when joined to type IV gold or silver-palladium-copper alloys, which was speculated to result primarily from interactions between the thione or thiol groups and copper elements contained in both alloys 10,13,19) . Previous studies have reported that the bonding mechanism of the VTD monomer to noble metal alloys involves an ionic interaction between mercapto groups in the VTD and metal ions in the alloys, especially gold, silver, or copper 33,34) . With respect to the bonding mechanism of the MDDT monomer with pure gold, Ikemura et al suggested that the cyclic disulfide group is cleaved at the disulfide bond or ring-opening and interacts with the gold atoms to form a sulfur-gold bond at the metal surface 15,18) .…”

Bonding performance of a thiohydantoin-methacrylate monomer on noble metal alloys

“…The VP contained VBATDT monomer. MP was synthesized according to a previously described method 13) . Both primers were of a single liquid type and contained one adhesive monomer in the acetone.…”

“…In 2020, the synthesis of a novel sulfur-containing monomer, 10-methacryloyloxydecyl-(2-thiohydantoin-4-yl) propionate (MDTHP), was reported 13) . MDTHP is a monomer containing thiohydantoin, a five membered heterocyclic compound with a thione structure.…”