Search Results (6)

This work aimed to synthesize a novel dimethacrylated-derivative of eugenol (Eg) (termed EgGAA) as potential biomaterial for certain applications such as dental fillings and adhesives. EgGAA was synthesized through a two-step reaction: (i) a mono methacrylated-eugenol (EgGMA) was produced via a ring-opening etherification of glycidyl methacrylate (GMA) with Eg; (ii) EgGMA was condensed with methacryloyl chloride into EgGAA. EgGAA was further incorporated in matrices containing BisGMA and TEGDMA (50:50 wt%) (TBEa), in which EgGAA replaced BisGMA as 0–100 wt% to get a series of unfilled resin composites (TBEa0–TBEa100), and by addition of reinforcing silica (66 wt%), a series of filled resins were also obtained (F-TBEa0–F-TBEa100). Synthesized monomers were analyzed for their structural, spectral, and thermal properties using FTIR, ¹H- and ¹³C-NMR, mass spectrometry, TGA, and DSC. Composites rheological and DC were analyzed. The viscosity (η, Pa·s) of EgGAA (0.379) was 1533 times lower than BisGMA (581.0) and 125 times higher than TEGDMA (0.003). Rheology of unfilled resins (TBEa) indicated Newtonian fluids, with viscosity decreased from 0.164 Pa·s (TBEa0) to 0.010 Pa·s (TBEa100) when EgGAA totally replaced BisGMA. However, composites showed non-Newtonian and shear-thinning behavior, with complex viscosity (η*) being shear-independent at high angular frequencies (10–100 rad/s). The loss factor crossover points were at 45.6, 20.3, 20.4, and 25.6 rad/s, indicating a higher elastic portion for EgGAA-free composite. The DC was insignificantly decreased from 61.22% for the control to 59.85% and 59.50% for F-TBEa25 and F-TBEa50, respectively, while the difference became significant when EgGAA totally replaced BisGMA (F-TBEa100, DC = 52.54%). Accordingly, these properties could encourage further investigation of Eg-containing resin-based composite as filling materials in terms of their physicochemical, mechanical, and biological potentiality as dental material. Full article

The aim of this work was to assess the limiting rate of eugenol (Eg) and eugenyl-glycidyl methacrylate (EgGMA) at which the ideal degree of conversion (DC) of resin composites is achieved. For this, two series of experimental composites, containing, besides reinforcing silica and a photo-initiator system, either EgGMA or Eg molecules at 0–6.8 wt% per resin matrix, principally consisting of urethane dimethacrylate (50 wt% per composite), were prepared and denoted as UGx and UEx, where x refers to the EgGMA or Eg wt% in the composite, respectively. Disc-shaped specimens (5 × 1 mm) were fabricated, photocured for 60 s, and analyzed for their Fourier transform infrared spectra before and after curing. The results revealed concentration-dependent DC, increased from 56.70% (control; UG0 = UE0) to 63.87% and 65.06% for UG3.4 and UE0.4, respectively, then dramatically decreased with the concentration increase. The insufficiency in DC due to EgGMA and Eg incorporation, i.e., DC below the suggested clinical limit (>55%), was observed beyond UG3.4 and UE0.8. The mechanism behind such inhibition is still not fully determined; however, radicals generated by Eg may drive its free radical polymerization inhibitory activity, while the steric hindrance and reactivity of EgGMA express its traced effect at high percentages. Therefore, while Eg is a severe inhibitor for radical polymerization, EgGMA is safer and can be used to benefit resin-based composites when used at a low percentage per resin. Full article

The present study aimed to evaluate the properties of new dental formulations incorporating a new polymerizable-derivative of eugenol (EgGMA). The experimental composites were prepared (by weight) with 35% resin-based matrix (1:1, bisphenol A-glycidyl methacrylate/triethylene glycol dimethacrylate) and 65% reinforcing materials (4:3, hydroxyapatite/zirconium oxide). A portion of 0.0, 2.5, and 5.0% of the resins with respect to the total composite was replaced by EgGMA monomer to obtain TBEg0, TBEg2.5, and TBEg5, respectively. The complex viscosity (at 25 and 37 °C), degree of conversion (DC), and water sorption (W_SP) and water solubility (W_SL) (3 cycles of sorption-desorption process) were investigated. Data were statistically analyzed using one-way and Tukey post-hoc tests. The results revealed a viscosity reduction with shear-thinning behavior as the EgGMA amount and temperature increased. The average complex viscosities at a lower frequency (ω = 1.0 rad/s) and at 25 °C were 234.7 ± 13.4, 86.4 ± 16.5, and 57.3 ± 17.1 (kPa·s) for TBEg0, TBEg2.5, and TBEg5, respectively. The inclusion of EgGMA led to a lower DC and W_SP but higher W_SL, compared to those of the reference (TBEg0). However, no significant differences between TBEg2.5 and control were detected (p > 0.05). Therefore, the incorporation of EgGMA in a low quantity, e.g., up to 8.45 mol% of resins, within the matrix may enhance the composite’s performance, including handling and solubility properties without any apparent effect on DC and water sorption, making it a promising monomeric biomaterial for various applications including restorative dentistry. Full article

The aim of this study was to evaluate the properties of new dental formulations containing eugenyl-2-hydroxypropyl methacrylate (EgGMA) monomer, as restorative dental material, in terms of their degree of photopolymerization and cytotoxicity. The target model composites (TBEg0, TBEg2.5, and TBEg5) were prepared by mixing 35% organic matrix (TEGDMA/BisGMA (50/50 wt%) of which 0, 2.5, and 5 wt%, respectively, were replaced with EgGMA monomer) with 65% filler (silanized hydroxyapatite (HA)/zinc oxide (ZnO₂), 4:3 by weight). The vinylic double-bond conversion (DC) after light-curing was studied using Fourier transform infrared technique whereas cell viability was in vitro tested using primary human gingival fibroblasts cells over 7 days by means of AlamarBlue colorimetric assay. The obtained data were statistically analyzed using ANOVA and Tukey post-hoc tests. The results revealed no significant difference in DC between TBEg2.5 (66.49%) and control (TBEg0; 68.74%), whereas both differ significantly with TBEg5, likely due to the inhibitory effect of eugenol moiety at high concentration. The cell viability test indicated that all the composites are biocompatible. No significant difference was counted between TBEg2.5 and TBEg5, however, both differed significantly from the control (TBEg0). Thus, even though its apparent negative effect on polymerization, EgGMA is potentially safer than bisphenol-derived monomers. Such potential properties may encourage further investigations on term of EgGMA amount optimization, compatibility with other dental resins, and antimicrobial activity. Full article

Biobased monomers have been used to replace their petroleum counterparts in the synthesis of polymers that are aimed at different applications. However, environmentally friendly polymerization processes are also essential to guarantee greener materials. Thus, photoinduced polymerization, which is low-energy consuming and solvent-free, rises as a suitable option. In this work, eugenol-, isoeugenol-, and dihydroeugenol-derived methacrylates are employed in radical photopolymerization to produce biobased polymers. The polymerization is monitored in the absence and presence of a photoinitiator and under air or protected from air, using Real-Time Fourier Transform Infrared Spectroscopy. The polymerization rate of the methacrylate double bonds was affected by the presence and reactivity of the allyl and propenyl groups in the eugenol- and isoeugenol-derived methacrylates, respectively. These groups are involved in radical addition, degradative chain transfer, and termination reactions, yielding crosslinked polymers. The materials, in the form of films, are characterized by differential scanning calorimetry, thermogravimetric, and contact angle analyses. Full article

The radical-scavenging activities of the synthetic antioxidants 2-allyl-4-X-phenol (X=NO₂, Cl, Br, OCH₃, COCH₃, CH₃, t-(CH₃)₃, C₆H₅) and 2,4-dimethoxyphenol, and the natural antioxidants eugenol and isoeugenol, were investigated using differential scanning calorimetry (DSC) by measuring their anti-1,1-diphenyl-2-picrylhydrazyl (DPPH) radical activity and the induction period for polymerization of methyl methacrylate (MMA) initiated by thermal decomposition of 2,2'-azobisisobutyronitrile (AIBN) and benzoyl peroxide (BPO). 2-Allyl-4-methoxyphenol and 2,4-dimethoxy-phenol scavenged not only oxygen-centered radicals (PhCOO^.) derived from BPO, but also carbon-centered radicals (R^.) derived from the AIBN and DPPH radical much more efficiently, in comparison with eugenol and isoeugenol. 2-Allyl-4-methoxyphenol may be useful for its lower prooxidative activity. Full article