Evaluation of monomers derived from resorcinol as eluents of bisphenol A glycidyl dimethacrylate for the formulation of dental composite resins

Abstract

The objective of this work was to synthesize two bio-based monomers, using the resorcinol as raw material, and its effect as bisphenol A glycidyl dimethacrylate (Bis-GMA) eluents on different chemical-physical and biological properties of experimental photopolymerizable composite resins. The acrylic 1,3-phenylen diacrylic (1,3-FDA) and methacrylic 1,3-phenylen dimethacrylic (1,3-FDMA) monomers were synthesized and fully characterized through FTIR and 1 H-NMR spectroscopies. Experimental photopolimerizable composites were formulated using Bis-GMA/1,3-FDA or Bis-GMA/1,3-FDMA as organic matrix. The materials were compared with a Bis-GMA/TEGDMA resin-based composite used as control. Polymerization kinetics was evaluated by means of FTIR spectroscopy. Polymerization stress was directly measured through a polymerization stress tester. The cell viability of the composites was evaluated using the MTT assay. One-way analysis of variance and Tukey's test were used for statistical analysis. The materials formulated with the 1,3-FDA monomer showed higher Rp max values and lower polymerization stress values (p < 0.05), while the flexural strength, water sorption, and solubility remained similar to the TEGDMA composite. Conversely, the materials formulated with the 1,3-FDMA monomer showed a lower degree of conversion and statistically lower flexural strength (p < 0.05). All materials exhibited a cellular viability close to 100%. Concerning the study conditions, the acrylic 1,3-FDA monomer could be considered an alternative to TEGDMA in the formulation of photopolymerizable dental composite resins.

Manufacturing and photocrosslinking of a new bio‐based dimethacrylate resulting in hydrophobic crosslinked films

“…According to recent demands on more environmentally friendly and energy economic processes, the development of bio-based monomers and more energy-efficient light emitting diodes (LEDs) as radiation sources has received increased interest nowadays [7][8][9][10][11][12][13][14][15][16][17][18].…”

“…Therefore, renewable materials have attracted attention to replace materials originating from fossil sources. Furan dicarboxylic acid, limonene, nicotinic acid, resorcinol, oleic acid, d-fructose, and isosorbide depict examples for bio-based starting materials for methacrylate manufacturing [7][8][9][10][11][12][13][14][15][16]. Introduction of a methacrylate group into bio-based starting materials enables the application of wellknown polymerization mechanisms on the one hand and consequently stepwise substitution of fossil resources by renewable starting materials on the other hand.…”

“…Dimethacrylates are established monomers in photopolymerizing mixtures that have been used for the manufacturing of protecting coatings, printing plates, printing inks, three‐dimensional printing systems, tissue‐engineering matrixes, and dental composites [1–6]. According to recent demands on more environmentally friendly and energy economic processes, the development of bio‐based monomers and more energy‐efficient light emitting diodes (LEDs) as radiation sources has received increased interest nowadays [7–18]. Therefore, renewable materials have attracted attention to replace materials originating from fossil sources.…”

NIR-sensitized hybrid radical and cationic photopolymerization of several cyanines in combination with diaryliodonium bis(trifluoromethyl)sulfonyl imide

“…[1][2][3][4][5][6] Emerging applications can be seen in printing with a focus on 2D, 7 3D 2,8,9 or 4D 2,[9][10][11] patterning, protection of sensitive surfaces such as paper, wood, and textiles, [12][13][14] and dental restoration. 15,16 Most of these systems worked in combination with traditional mercury lamps or UV/blue light LEDs. UV-photoinitiating systems exhibit the highest sensitivity while their absorption in UV-A often restricts their use for much broader application viewpoints.…”

The Development of Filler Morphology in Dental Resin Composites: A Review

“…After curing, the resin matrix forms a three-dimensional network structure to encapsulate fillers. And fillers have usually been treated with a coupling agent to improve the bonding and stress transfer between fillers and the matrix [ 7 ]. Since DRC shrinkage after curing seems to result from resin matrix polymerization, much research has focused on the modification of the resin matrix.…”