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. 2014 Oct;102(7):1473-84.
doi: 10.1002/jbm.b.33126. Epub 2014 Mar 5.

Synthesis and evaluation of novel dental monomer with branched carboxyl acid group

Linyong Song  1 , Qiang Ye, Xueping Ge, Anil Misra, Jennifer S Laurence, Cynthia L Berrie, Paulette Spencer
Affiliations

Synthesis and evaluation of novel dental monomer with branched carboxyl acid group

Linyong Song et al. J Biomed Mater Res B Appl Biomater. 2014 Oct.

Abstract

To enhance the water miscibility and increase the mechanical properties of dentin adhesives, a new glycerol-based monomer with vinyl and carboxylic acid, 4-((1,3-bis(methacryloyloxy)propan-2-yl)oxy)-2-methylene-4-oxobutanoic acid (BMPMOB), was synthesized and characterized. Dentin adhesive formulations containing 2-hydroxyethyl methacrylate (HEMA), 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy) phenyl]propane (BisGMA), and BMPMOB were characterized with regard to real-time photopolymerization behavior, water sorption, dynamic mechanical analysis, and microscale three-dimensional internal morphologies and compared with HEMA/BisGMA controls. The experimental adhesive copolymers showed higher glass transition temperature and rubbery moduli, as well as improved water miscibility compared to the controls. The enhanced properties of the adhesive copolymers indicated that BMPMOB is a promising comonomer for dental restorative materials.

Keywords: crosslink polymer; dentin adhesive; dynamical mechanical property; photopolymerization; water miscibility.

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Figures

FIGURE 1
FIGURE 1
Reaction scheme for synthesis of BMPMOB.
FIGURE 2
FIGURE 2
FTIR (A), 1H-NMR (B), and 13C-NMR (C) spectra in CDCl3 of BMPMOB. EA: ethyl acetate. [Color figure can be viewed in the online issue, which is available at wileyonlinelibrary.com.]
FIGURE 3
FIGURE 3
Relation between mole averaged log P and water miscibility of adhesive formulations, water sorption of copolymers contained BMPMOB. Wwm stands for water miscibility, and Wsp stands for water sorption. (■ represents the water miscibility value of liquid formulation; ▨ represents the water sorption of copolymer beam specimen, ⋄ represents the difference between water miscibility of liquid formulation and water sorption of copolymer, ΔW = Wwm − Wsp). [Color figure can be viewed in the online issue, which is available at wileyonlinelibrary.com.]
FIGURE 4
FIGURE 4
The microscale morphologies of the control (A1: CT slice at the x–y plane from the 3D image, A2: 3D image) and experimental E1-25 formulation (B1: CT slice at x–y plane from 3D image, B2: 3D image) adhesive copolymer prepared in the presence of 13 wt % water. [Color figure can be viewed in the online issue, which is available at wileyonlinelibrary.com.]
FIGURE 5
FIGURE 5
Real-time conversion (A) and comparison of polymerization rates (B) of control (C0 and C1) and experimental adhesives (E1-15, E1-25, and E1-35). The adhesives were light-cured for 40 s at RT using a commercial visible light lamp (Spectrum® 800; Dentsply, Milford, DE. Intensity is 550 mW cm−2). *Significantly (p < 0.05) different from the control (C0). [Color figure can be viewed in the online issue, which is available at wileyonlinelibrary.com.]
FIGURE 6
FIGURE 6
Water sorption of adhesive copolymers with time (A) and the final solubility and water sorption after storage in water at 25°C for 9 days (B). [Color figure can be viewed in the online issue, which is available at wileyonlinelibrary.com.]
FIGURE 7
FIGURE 7
Representative storage modulus (A and B), derivative storage modulus (C and D), and tan δ (E and F) versus temperature curves of the control and experimental adhesive copolymers in dry (A, C, and E) and wet (B, D, and F) condition. [Color figure can be viewed in the online issue, which is available at wileyonlinelibrary.com.]
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