Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 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.

PubMed Disclaimer

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.]
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Tjaderhane L, Nascimento FD, Breschi L, Mazzoni A, Tersariol ILS, Geraldeli S, Tezvergil-Mutluay A, Carrilho M, Carvalho RM, Tay FR, Pashley DH. Strategies to prevent hydrolytic degradation of the hybrid layer—A review. Dent Mater. 2013;29(10):999–1011. - PMC - PubMed
    1. Burrow MF, Satoh M, Tagami J. Dentin bond durability after three years using a dentin bonding agent with and without priming. Dent Mater. 1996;12(5–6):302–307. - PubMed
    1. Hashimoto M, Ohno H, Kaga M, Endo K, Sano H, Oguchi H. In vivo degradation of resin-dentin bonds in humans over 1 to 3 years. J Dent Res. 2000;79(6):1385–1391. - PubMed
    1. Hashimoto M, Ohno H, Sano H, Tay FR, Kaga M, Kudou Y, Oguchi H, Araki Y, Kubota M. Micromorphological changes in resin–dentin bonds after 1 year of water storage. J Biomed Mater Res. 2002;63(3):306–311. - PubMed
    1. Sano H, Yoshikawa T, Pereira PNR, Kanemura N, Morigami M, Tagami J, Pashley DH. Long-term durability of dentin bonds made with a self-etching primer, in vivo. J Dent Res. 1999;78(4):906–911. - PubMed

Publication types

MeSH terms

LinkOut - more resources