title: Investigation on synthesis and properties of isosorbide based bis-GMA analogue.
abstract: The aim of this work was to synthesize and investigate properties of a novel dimethacrylic monomer based on bioderived alicyclic diol--isosorbide. Its potential as a possible substitute of 2,2-bis[4-(2-hydroxy-3-methacryloyloxypropoxy)phenyl]propane (BISGMA), widely used in dental restorative materials and suspected for toxicity was assessed. The novel monomer was obtained in a three-step synthesis. First, isosorbide was etherified by a Williamson nucleophilic substitution and subsequently oxidized to isosorbide diglycidyl ether (ISDGE). A triphenyl phosphine catalyzed addition of methacrylic acid to ISDGE resulted in 2,5-bis(2-hydroxy-3-methacryloyloxypropoxy)- 1,4:3,6-dianhydro-sorbitol (ISDGMA). The monomer obtained was photopolymerized using camphorquinone/2-(dimethylamino)ethyl methacrylate initiating system. Next, compositions with triethylene glycol dimethacrylate (TEGDMA) were prepared and polymerized. Double bond conversion, polymerization shrinkage and water sorption of resulting polymers were determined. Selected mechanical (flexular strength and modulus, Brinell hardness) and thermomechanical (DMA analysis) properties were also investigated. BISGMA based materials were prepared as reference for comparison of particular properties.
authors.affiliation: Faculty of Chemistry, Department of Physical Chemistry and Technology of Polymers, Silesian University of Technology, ul. M. Strzody 9, 44-100 Gliwice, Poland. Jan.Lukaszczyk@polsl.pl
authors.forename: Jan
authors.initials: J
authors.lastname: Łukaszczyk
authors.forename: Bartosz
authors.initials: B
authors.lastname: Janicki
authors.forename: Achim
authors.initials: A
authors.lastname: Frick
mesh_terms: D000327:Adsorption; D001696:Biomechanical Phenomena; D017438:Bisphenol A-Glycidyl Methacrylate / Q000138:chemical synthesis / Q000737:chemistry*; D003188:Composite Resins / Q000138:chemical synthesis / Q000737:chemistry; D003764:Dental Materials / Q000138:chemical synthesis* / Q000737:chemistry*; D055119:Elastic Modulus; D006244:Hardness / Q000502:physiology; D007547:Isosorbide / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008422:Materials Testing; D008954:Models, Biological; D058105:Polymerization; D013046:Specific Gravity; D014867:Water / Q000378:metabolism; D017155:Wettability
chemical_list: D003188:Composite Resins; D003764:Dental Materials; D014867:Water; D017438:Bisphenol A-Glycidyl Methacrylate; D007547:Isosorbide