Novel 1,2-Bismethacrylate-3-Eugenyl Propane for Resin Composites: Synthesis, Characterization, Rheological, and Degree of Conversion

Haifa Masfeer Al-Kahtani; Abdel-Basit Al-Odayni; Waseem Sharaf Saeed; Ali Robaian; Abdullah Al-Kahtani; Taieb Aouak; Ali Alrahlah

doi:10.3390/polym15061481

Novel 1,2-Bismethacrylate-3-Eugenyl Propane for Resin Composites: Synthesis, Characterization, Rheological, and Degree of Conversion

Polymers (Basel). 2023 Mar 16;15(6):1481. doi: 10.3390/polym15061481.

Authors

Haifa Masfeer Al-Kahtani¹, Abdel-Basit Al-Odayni^{2

3}, Waseem Sharaf Saeed², Ali Robaian⁴, Abdullah Al-Kahtani¹, Taieb Aouak¹, Ali Alrahlah^{2

5}

Affiliations

¹ Chemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
² Engineer Abdullah Bugshan Research Chair for Dental and Oral Rehabilitation, College of Dentistry, King Saud University, Riyadh 11545, Saudi Arabia.
³ Department of Chemistry, Faculty of Education, Thamar University, Dhamar 87246, Yemen.
⁴ Conservative Dental Sciences Department, College of Dentistry, Prince Sattam Bin Abdulaziz University, Alkharj 11942, Saudi Arabia.
⁵ Restorative Dental Sciences Department, College of Dentistry, King Saud University, Riyadh 11545, Saudi Arabia.

Abstract

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.

Keywords: degree of conversion; dental composite; dimethacrylated derivative; eugenol; eugenol derivative; resin; rheology.

Grants and funding

This research was funded by the Deanship of Scientific Research, King Saud University through the Vice Deanship of Scientific Research Chairs, Engineer Abdullah Bugshan research chair for Dental and Oral Rehabilitation.