Dental composite resins with low polymerization stress based on a new allyl carbonate monomer

The objective of this study was to synthesize a diallyl carbonate monomer, allyl(2-(2-(((allyloxy)carbonyl)oxy)benzoyl)-5-methoxyphenyl) carbonate (BZ-AL), and to evaluate its effect as Bis-GMA diluent in the formulation of photopolymerizable dental composite resins. The chemical structure of BZ-AL monomer was determined by means of H¹ NMR, C¹³ NMR and FTIR spectroscopies. An experimental composite comprising a mixture of Bis-GMA and BZ-AL monomers and silanized inorganic filler was formulated. Experimental material was compared with a control composite formulated with Bis-GMA/TEGDMA. Double bond conversion, polymerization kinetics, volumetric shrinkage, polymerization stress, and flexural properties were investigated. The data were analyzed through a Student t-test (α = 0.05). Flexural strength of the experimental materials with BZ-AL monomer showed a statistically significant increase (p < 0.001). The experimental composite has a lower polymerization rate than the control composite, on the other hand, the experimental composite resin has the highest degree of double bond conversion. There are no differences in the polymerization shrinkage of the composites, however, the polymerization stress of the experimental materials was 50% lower than the control resin. Finally, the cell viability test showed that the experimental resins formulated with the BZ-AL monomer was not cytotoxic. Due to its characteristics, BZ-AL monomer is potentially useful for the formulation of composite materials with applications in dentistry.