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A Low-Viscosity Bisgma Derivative for Resin Composites: Synthesis, Characterization, and Evaluation of Its Rheological Properties

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A Low-Viscosity Bisgma Derivative for Resin Composites: Synthesis, Characterization, and Evaluation of Its Rheological Properties materials Article A Low-Viscosity BisGMA Derivative for Resin Composites: Synthesis, Characterization, and Evaluation of Its Rheological Properties Ali Alrahlah 1,2,* , Abdel-Basit Al-Odayni 2,* , Haifa Fahad Al-Mutairi 2, Bashaer Mousa Almousa 2, Faisal S. Alsubaie 3 , Rawaiz Khan 2 and Waseem Sharaf Saeed 2 1 Restorative Dental Sciences Department, College of Dentistry, King Saud University, Riyadh 11545, Saudi Arabia 2 Engineer Abdullah Bugshan Research Chair for Dental and Oral Rehabilitation, College of Dentistry, King Saud University, Riyadh 11545, Saudi Arabia; [email protected] (H.F.A.-M.); [email protected] (B.M.A.); [email protected] (R.K.); [email protected] (W.S.S.) 3 Chemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia; [email protected] * Correspondence: [email protected] (A.A.); [email protected] (A.-B.A.-O.) Abstract: This study aimed to synthesize new bisphenol A-glycidyl methacrylate (BisGMA) deriva- tives, targeting a reduction in its viscosity by substituting one of its OH groups, the leading cause of its high viscosity, with a chlorine atom. Hence, this monochloro-BisGMA (mCl-BisGMA) monomer was synthesized by Appel reaction procedure, and its structure was confirmed using Fourier transform infrared spectroscopy, 1H and 13C-nuclear magnetic resonance spectroscopy, and mass spectroscopy. The viscosity of mCl-BisGMA (8.3 Pa·s) was measured under rheometry conditions, and it was found to be more than 65-fold lower than that of BisGMA (566.1 Pa·s) at 25 ◦C. For the assessment of the viscosity changes of model resins in the presence of mCl-BisGMA, a series of resin matrices, in which, besides BisGMA, 50 wt % was triethylene glycol dimethacrylate, were prepared and evaluated ◦ Citation: Alrahlah, A.; Al-Odayni, at 20, 25, and 35 C. Thus, BisGMA was incrementally replaced by 25% mCl-BisGMA to obtain A.-B.; Al-Mutairi, H.F.; Almousa, TBC0, TBC25, TBC50, TBC75, and TBC100 blends. The viscosity decreased with temperature, and B.M.; Alsubaie, F.S.; Khan, R.; Saeed, the mCl-BisGMA content in the resin mixture increased. The substantial reduction in the viscosity W.S. A Low-Viscosity BisGMA value of mCl-BisGMA compared with that of BisGMA may imply its potential use as a dental resin Derivative for Resin Composites: matrix, either alone or in combination with traditional monomers. However, the various properties Synthesis, Characterization, and of mCl-BisGMA-containing matrices should be evaluated. Evaluation of Its Rheological Properties. Materials 2021, 14, 338. Keywords: BisGMA derivative; dental resin composite; monomer viscosity; dental material; rheometry https://doi.org/10.3390/ma14020338 Received: 21 December 2020 Accepted: 8 January 2021 Published: 11 January 2021 1. Introduction Dental caries is one of the most common chronic diseases throughout the life span. Publisher’s Note: MDPI stays neu- Although it is largely preventable, it is still a major public health problem worldwide [1]. tral with regard to jurisdictional clai- Restorative dental materials used to fill dental cavities are usually metals, ceramics, poly- ms in published maps and institutio- mers, or composites [2]. Photocurable resin-based composites are the common choice for nal affiliations. patients and practitioners due to their superior aesthetics and easy handling and shap- ing properties [3]. Therefore, they increasingly became popular in dentistry. Generally, resin-based composites comprise resin matrix, reinforcing fillers, filler–matrix interface coupling agents, and polymerization initiator systems; however, the last two are usually Copyright: © 2021 by the authors. Li- censee MDPI, Basel, Switzerland. incorporated in traces (<1 wt %). Resins are conventionally photocurable acrylate-based This article is an open access article monomers, which represent one major influencer of the final properties of filling com- distributed under the terms and con- posites. Matrices of commercial dental composites predominantly consist of bisphenol ditions of the Creative Commons At- A-glycidyl methacrylate (BisGMA) monomer [4–6]. However, other dimethacrylates, such tribution (CC BY) license (https:// as urethane dimethacrylate (UDMA), ethoxylated bisphenol A dimethacrylate (BisEMA), creativecommons.org/licenses/by/ and triethylene glycol dimethacrylate (TEGDMA), are also common constituents of the 4.0/). resin matrix [7,8]. Materials 2021, 14, 338. https://doi.org/10.3390/ma14020338 https://www.mdpi.com/journal/materials Materials 2021, 14, 338 2 of 15 BisGMA is a good choice as a base matrix for hosting composite constituents. It has strong advantages over its (di)(meth)acrylate-based analogs, including its low polymer- ization shrinkage, suitable mechanical properties, relatively high refractive index, and excellent adhesion to enamel [9,10]. The major disadvantage of BisGMA is its high vis- cosity [9], which prevents the addition of high contents of fillers. On the molecular level, BisGMA has a stiff central aromatic core and two hydroxyl groups that kinetically cause a reduced degree of molecular freedom. Hydrogen bonds are said to be the major player in the degree of intermolecular interaction; thus, they increase the viscosity of the monomer, reduce its chains’ mobility, and make it difficult to mix with other ingredients, resulting in a reduced degree of conversion (DC) upon polymerization. These impair the overall integrity and longevity of the restorative materials; in particular, the mechanical properties are significantly weakened. The viscosity of the matrix is of great importance and is strictly associated with certain features of the composite, either before or after application [11]. The high viscosity of the matrix may limit the amounts of reinforcing materials, generate handling difficulties, reduce DC, weaken composite mechanical properties, and reduce its longevity. It is directly linked to the chemical structure of monomeric constituents; thus, it is an indicator of the degree of intermolecular interactions at the molecular level. However, the viscosity of BisGMA (910 Pa·s, at ~22 ◦C) [12] is the highest among the other common dimethacrylate monomers used in resin-based dental composite due to its large molecular weight and strong molecular interactions driven by H-bonding. To overcome the drawbacks correlated with the high viscosity of BisGMA, the matrix is usually diluted with TEGDMA (0.01 Pa·s, at ~22 ◦C) as a suitable low-viscosity diluent [12]. However, TEGDMA enhances the hydrophilicity characters of the composite, which further increases the undesirable water sorption and polymerization shrinkage. Additionally, (di)(multi)functional monomers form cross-linked networks, which causes a remarkable decrease in DC upon curing. As polymerization proceeds, the movement of the macro- radicals becomes more restricted, and thereafter, diffusion-controlled process being the dominant mechanism of propagation and termination [6,13]. To obtain suitable low-viscose monomers, scientists have synthesized different BisGMA-alike monomers [7,9]. Others tried the fabrication of the BisGMA chemical structure by, for example, synthesizing various derivatives [5,12,14–17]; however, reaching the state-of-the-art monomer with low viscosity and superior properties for dental restorations is one current objective for specialists. In this regard, the replacement of the hydroxyl groups in BisGMA by, e.g., less- hydrophilic groups, is one possible solution to tailor its viscosity, i.e., by limiting the degree of molecular interaction caused by H-bonding. Examples of these organic groups include –CH3 [16], –CF3 [17], –OCH3 [15], –OCOCH2C6H5 and –C4H9 [14], and –Cl [12]. In the lat- ter case, Al-Odayni et al. [12] synthesized a new BisGMA derivative (Cl-BisGMA, hereafter termed as dCl-BisGMA) in which the two hydroxyls were substituted by chlorine atoms. Remarkable enhancements in the viscosity, DC, and water sorption were reported after modification. However, of the studied properties, water solubility was increased. Addi- tionally, the initial biological evaluation of dCl-BisGMA, assessed through cell viability and live/dead assays and cell attachment tests using immortalized human bone marrow stromal cells, revealed biocompatible characters, encouraging further investigations. Fur- ther, targeting only one hydroxyl group from the two in BisGMA may sufficiently decrease its viscosity and additionally, retain its desirable properties. The objective of this work is to develop a new BisGMA derivative in which one hy- droxyl is replaced by a chlorine atom. It is expected that the replacement of one hydroxyl group would significantly reduce viscosity. Compared with BisGMA and dCl-BisGMA, monochloro-BisGMA (mCl-BisGMA) should possess greater advantages. It was synthe- sized using chemically controlled reaction conditions; one –OH group was targeted for substitution, and afterward, its structure was fully characterized using Fourier transform infrared (FTIR), 1H and 13C-nuclear magnetic resonance (NMR) spectroscopy, and mass Materials 2021, 14, 338 3 of 15 spectroscopy (MS). The viscosities of mCl-BisGMA alone and in a mixture with BisGMA and TEGDMA were also evaluated at different temperatures. 2. Materials and Methods 2.1. Materials BisGMA (>98%), TEGDMA (>95%), 2-(N, N-dimethyl amino) ethyl-methacrylate (98%), camphorquinone (97%), and carbon tetrachloride (CCl4; >99.8%) were procured from Sigma-Aldrich, Darmstadt, Germany. Triphenylphosphine (Ph3P; >98%) was purchased from Cica-reagent
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