Biobased isosorbide methacrylate monomer as an alternative to bisphenol A glycerolate dimethacrylate for dental restorative applications

Abstract

In this study, a new biobased isosorbide urethane methacrylic monomer [isosorbide‐derived urethane dimethacrylate (Is‐UDMA)] was evaluated as a replacement for currently used bisphenol A glycerolate dimethacrylate (Bis‐GMA) based dental restorative materials. Dental composites were prepared at different Is‐UDMA and Bis‐GMA concentrations. For these composites, the photocuring kinetics, volumetric shrinkage, viscoelastic properties, water sorption, and solubility were evaluated. The photocuring kinetics, followed by real‐time IR spectroscopy, showed higher double‐bond conversion (DC) values for the formulations containing the Is‐UDMA monomer; the highest DC (82%) was achieved by the formulation prepared with only the Is‐UDMA monomer. The volumetric shrinkage was reduced to 23.7% as compared with the dental resin formulated with Bis‐GMA. The viscoelastic properties of the formulations containing both Is‐UDMA and Bis‐GMA monomers in a 50:50 composition were superior to the rest of the tested formulations, including those prepared with pure polymers. This behavior was explained in terms of a compromise between crosslinking and rigidity (or flexibility) of the resulting polymer network. A preliminary test on microleakage in a dental enamel demonstrated that the new Is‐UDMA monomer is a potential replacement for the Bis‐GMA monomer in dental restorative materials. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44591.

Future opportunities for bio-based adhesives – advantages beyond renewability

“…37 Another example in which an adhesive based on a biobased monomer showed better properties than the previous, non-bio-based solution was reported by Berlanga Duarte et al and concerned dental fillers. 108 The bio-based monomer isosorbide was modified with isophorone diisocyanate and hydroxyethylmethacrylate (HEMA) and compared to the traditional matrix material bisphenol A glycerolate dimethacrylate (bis-GMA) as shown in Fig. 20 and 21.…”

“…Higher adhesive strength Polyurethane from palm oil polyol, 104 polyurethane from partially bio-based isocyanate and castor oil, 38 polyurethane based on castor oil, 106 polyether-polyester based on canola oil, 37 protein-urea formaldehyde mixture for particle boards 109 Better chemical resistance Polyurethane from canola oil and 1,3-propanediol polyol 73 Lower volume reduction Isosorbide-based dental adhesive 108…”

Dental restorative composites containing methacrylic spiroorthocarbonate monomers as antishrinking matrixes

“…The photoinitiator was a mixture of CQ, DAB, and DPPI. The compositions of the dental formulations are summarized in Tables and …”

Hydrophobically Modified Isosorbide Dimethacrylates as a Bisphenol-A (BPA)-Free Dental Filling Material

“…It is made up of two cis -fused tetrahydrofuran rings, which are nearly planar, and contains two hydroxyls at positions 2 and 5, as shown in Figure 1 [ 20 , 21 ]. Isosorbide has found potential applications in the biomedical field, including aspirin prodrugs [ 22 , 23 ], substrates for human butyrylcholinesterase [ 24 ], tissue engineering scaffolds [ 25 , 26 ], and dental restorative materials [ 27 , 28 , 29 , 30 ].…”

“…Some of the studies on isosorbide for dental materials include the synthesis and evaluation of the BisGMA analogue, 1,4:3,6-dianhydro- d -sorbitol 2,5-bis(2-hydroxy-3-methacylolxypropoxy) (ISDGMA) as reported by Łukaszczyk et al, and Shin and coworkers [ 27 , 28 ]. Duarte et al, have studied the synthesis of an isosorbide urethane dimethacrylate (IS-UDMA) [ 29 ]. Vasifihasel et al and Łukaszczyk and co-workers developed ethoxylated isosorbide dimethacrylates (ISETDMA) as a dental diluent [ 30 , 31 ].…”