title: Synthesis of glycerol-derived diallyl spiroorthocarbonates and the study of their antishrinking properties in acrylic dental resins.
abstract: In this work was evaluated the efficiency of an antishrinkage additive in a dental resin. This additive was a mixture 1:1 of five and six-membered ring spiroorthocarbonates functionalized with allylic groups (SOC DA). The aim of this study was to reduce the shrinkage of a typical dental resin composed of a blend of the dimethacrylates, Glycerolate bisphenol A dimethacrylate (Bis-GMA)/2-[(3,5,5-trimethyl-6-[2-(2-methyl prop-2-enoyloxy) ethoxycarbonylamino] hexyl) carbamoyloxy] ethyl, 2-methyl prop-2-enoate, (UDMA)/triethyleneglycol dimethacrylate (TEGDMA) in a 50:30.20 molar ratio, and silicon dioxide as filler. SOC DA was added at 5, 10 and 20 mol% to the already mentioned formulation. It was found that the addition of 20 mol% of SOC DA decreased 53 % the shrinkage of the cured composite material, in comparison with a formulation where it was not added the antishrinkage additive. Besides, the kinetics of photopolymerization determined by Real-Time infrared spectroscopy, demonstrated that the addition of increasing concentration of SOC DA improved the conversion of double bonds of dimethacrylates. Additionally, the presence of SOC DA at 10 % mol, helped to increase the flexural strength and the compressive strength of the composite, as a consequence of the augment of the crosslink density, induced by the ring opening polymerization of SOC DA.
authors.affiliation: Centro de Investigación en Química Aplicada, Blvd. Enrique Reyna Hermosillo No. 140, CP 25253, Saltillo, Coahuila, Mexico. ricardo.acosta@ciqa.edu.mx
authors.forename: Ricardo
authors.initials: R
authors.lastname: Acosta Ortiz
authors.forename: Luis Alberto
authors.initials: LA
authors.lastname: Reyna Medina
authors.forename: María Lydia
authors.initials: ML
authors.lastname: Berlanga Duarte
authors.forename: Lucía
authors.initials: L
authors.lastname: Ibarra Samaniego
authors.forename: Aida Esmeralda
authors.initials: AE
authors.lastname: Garcia Valdez
authors.forename: Zaida Lucía
authors.initials: ZL
authors.lastname: García Mendez
authors.forename: Luis
authors.initials: L
authors.lastname: Mendez Gonzalez
mesh_terms: D000180:Acrylic Resins / Q000138:chemical synthesis / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry; D002254:Carbonates / Q000138:chemical synthesis* / Q000737:chemistry; D019245:Compressive Strength; D003799:Dental Stress Analysis; D005990:Glycerol / Q000737:chemistry*; D007700:Kinetics; D008422:Materials Testing; D008954:Models, Biological; D018583:Pliability; D058105:Polymerization; D017550:Spectroscopy, Fourier Transform Infrared; D013718:Tensile Strength
chemical_list: D000180:Acrylic Resins; D000498:Allyl Compounds; D002254:Carbonates; D005990:Glycerol