Photopolymerizable multifunctional monomers and their evaluation as reactive Bis‐GMA eluents

Abstract

Bis‐GMA {2,2‐bis[4‐(2′‐hydroxy‐3′‐methacryloyloxy‐propoxy)‐phenyl]‐propane}, TEGDMA <2‐{2‐[2‐(2‐methylprop‐2‐enoyloxy)ethoxy]ethoxy}ethyl‐2‐methylprop‐2‐enoate>, and methyl methacrylate (MMA) are some of the most commonly used monomers in the field of restorative dentistry. These compounds are characterized by having one or two terminal double bonds. Besides the effort to synthesize new monomers, several problems still affect the clinical behavior of contemporary dental materials. In this work, two monomers with three terminal double bonds, 5A13DA and 5A13DMA, were synthesized. Both monomers were used to completely replace TEGDMA as reactive diluent of photopolymerizable dental resin composites containing Bis‐GMA. The effects of 5A13DA and 5A13DMA on flexural properties, double bond conversion, water sorption, solubility, and polymerization shrinkage were evaluated. In addition, both monomers were evaluated as crosslinking agents for methylmethacrylate, resulting in copolymers with enhanced thermal stability. The results obtained suggest that newly synthesized monomers are potential substitutes for TEGDMA in the formulation of dental composites, providing 50% lower volumetric shrinkage than the composite resin used as control and adequate mechanical properties. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46240.

Analysis of Double Bond Conversion of Photopolymerizable Monomers by FTIR-ATR Spectroscopy

“…Such techniques are able to detect the stretching vibration of carbon–carbon double bonds involved in the polymerization process . Recently, FTIR spectroscopy was used for the determination of the degree of double bond conversion of experimental dental composite resins based on these types of monomers. − …”

Dental resin composites: A review on materials to product realizations

“…The developed monomers showed many interesting mechanical and physical characteristics as summarized in Table 1 and the related chemical structure of the emerging diluent monomers are presented in Figure 2. These studies showed the enhanced properties of low volume shrinkage and shrinkage stress without compromising mechanical and biological properties to act as a viable candidate to replace TEGDMA, including aromatic methacrylates [60], triethylene glycol divinylbenzyl ether (TEG-DVBE) [61], diallyl(5-(hydroxymethyl)-1,3phenylene) decarbonate (HMFBA) and 5-(hydroxymethyl)-1,3-phenylene bis(2methylacrylate (HMFBM) [62], diallyl (propane-2,2-diylbis (1,4-phenylene)) biscarbonate (BPhADAC) [63], allyl(2-(2-(((allyloxy)carbonyl)oxy)benzoyl)-5-methoxyphenyl) carbonate (BZ-AL) [64], trifunctional monomers (5A1603DA, 5A13DMA) [65], and n-methyl-bis(ethylcarbamate-isoproply-α-methylstyryl)amine (Phene) [66]. Especially, a new hydrolytically stable monomer, TEG-DVBE, was suggested as a good alternative to design a longer-lasting dental resin composite in water-rich oral environments.…”

Hydrophobic composite resins using a novel allylic urethane monomer as additive

“…Also, the use of spiroorthocarbonate monomers [12], siloranes [13] and ormocers [14,15] has been incorporated into dental composite formulations to produce composites with less polymerization shrinkage. Also, our workgroup has been working among the last years in the synthesis an evaluation of allylic monomers for dental composites application [16][17][18][19][20][21], obtaining promising results.…”