Synthesis and evaluation of novel dental monomer with branched aromatic carboxylic acid group

Abstract

A new glycerol-based dimethacrylate monomer with an aromatic carboxylic acid, 2-((1,3-bis(methacryloyloxy)propan-2-yloxy)carbonyl)benzoic acid (BMPB), was synthesized, characterized, and proposed as a possible dental co-monomer for dentin adhesives. Dentin adhesives containing 2-hydroxyethyl methacrylate (HEMA) and 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy) phenyl]propane (BisGMA) in addition to BMPB were formulated with water at 0, 5, 10, and 15 wt % to simulate wet, oral conditions, and photo-polymerized. Adhesives were characterized with regard to viscosity, real-time photopolymerization behavior, dynamic mechanical analysis, and microscale 3D internal morphologies and compared with HEMA/BisGMA controls. When formulated under wet conditions, the experimental adhesives showed lower viscosities (0.04–0.07 Pa s) as compared to the control (0.09–0.12 Pa s). The experimental adhesives showed higher glass transition temperature (146–157°C), degree of conversion (78–89%), and rubbery moduli (33–36 MPa), and improved water miscibility (no voids) as compared to the controls (123–135°C, 67–71%, 15–26 MPa, and voids, respectively). The enhanced properties of these adhesives suggest that BMPB with simple, straight-forward synthesis is a promising photocurable co-monomer for dental restorative materials.

Compositional design and optimization of dentin adhesive with neutralization capability

“…The decreasing maximum polymerization rates also supported the results. Many studies have shown that free radical polymerization of multifunctional methacrylates does not result in the complete conversion of C=C bonds and that the DCs are between 40 and 85% [10,16,38]. It has also been shown that the extent of cure (DC) influences the bulk physicochemical properties [35,39].…”

“…HEMA/BisGMA (45/55, w/w) was used as the control (C0) [10]. The experimental adhesive formulations consisting of HEMA, BisGMA, and MEMA are listed in Table 1.…”

“…The LA damages the adjacent tooth surface by demineralization. Although numerous monomers have been investigated [10–16], the lack of dentin adhesives that are both effective and durable continues to be a major problem in restorative dentistry. Different strategies have been developed to enhance the hydrolytic stability of dentin adhesive resins.…”

Synthesis and Evaluation of a Novel Co-Initiator for Dentin Adhesives: Polymerization Kinetics and Leachables Study

“…The kinetic data were converted to Rp/[M] 0 by taking the first derivative of the time versus conversion curve [12, 29, 30], where Rp and [M] 0 are the rate of polymerization and the initial monomer concentration, respectively.…”

Durable bonds at the adhesive/dentin interface:an impossible mission or simply a moving target?

“…[130,135] Methacrylate side chains have been selectively modified so that they were both water compatible and esterase resistant. [136][137][138][139][140]This was accomplished by using bulky and/ or branched functional groups that were poor esterase substrates but sufficiently hydrophilic to be water compatible. Water-compatible photoinitiators were developed as a means of promoting monomer/polymer conversion and thus, reducing the susceptibility to esterase hydrolysis by reducing the number of unreacted pendant groups [ 11,112,[141][142][143].…”