Enzyme-catalyzed hydrolysis of dentin adhesives containing a new urethane-based trimethacrylate monomer

A new trimethacrylate monomer with urethane‐linked groups, 1,1,1‐tri‐[4‐(methacryloxyethylamino‐carbonyloxy)‐phenyl]ethane (MPE), was synthesized, characterized, and used as a comonomer in dentin adhesives. Dentin adhesives containing 2‐hydroxyethyl methacrylate (HEMA, 45% w/w) and 2,2‐bis[4(2‐hydro...

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Bibliographic Details
Published in:Journal of biomedical materials research. Part B, Applied biomaterials Applied biomaterials, 2009-11, Vol.91B (2), p.562-571
Main Authors: Park, Jong-Gu, Ye, Qiang, Topp, Elizabeth M., Spencer, Paulette
Format: Article
Language:English
Subjects:
Absorbable Implants
Acrylic Resins - chemistry
Adhesiveness
Adhesives - chemistry
Dental Materials - chemistry
Dentin - chemistry
dentin adhesives
enzymatic degradation
Enzymes - chemistry
Esterases - chemistry
Hydrolysis
interface
Magnetic Resonance Spectroscopy
Materials Testing
Methylmethacrylates - chemistry
Microscopy, Electron, Scanning
photopolymerization
Staining and Labeling
Stress, Mechanical
Urethane - chemistry
urethane-based trimethacrylate
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Summary:A new trimethacrylate monomer with urethane‐linked groups, 1,1,1‐tri‐[4‐(methacryloxyethylamino‐carbonyloxy)‐phenyl]ethane (MPE), was synthesized, characterized, and used as a comonomer in dentin adhesives. Dentin adhesives containing 2‐hydroxyethyl methacrylate (HEMA, 45% w/w) and 2,2‐bis[4(2‐hydroxy‐3‐methacryloyloxy‐propyloxy)‐phenyl] propane (BisGMA, 30% w/w) in addition to MPE (25% w/w) were formulated with H2O at 0 (MPE0), 8 (MPE8), and 16 wt % water (MPE16) to simulate the wet demineralized dentin matrix and compared with controls [HEMA /BisGMA, 45/55 w/w, at 0 (C0), 8 (C8), and 16 wt % water (C16)]. The new adhesive showed a degree of double bond conversion and mechanical properties comparable with control, with good penetration into the dentin surface and a uniform adhesive/dentin interface. On exposure to porcine liver esterase, the net cumulative methacrylic acid (MAA) released from the new adhesives was dramatically (p < 0.05) decreased relative to the control, suggesting that the new monomer improves esterase resistance. © 2009 Wiley Periodicals, Inc. J Biomed Mater Res Part B: Appl Biomater 2009
ISSN:1552-4973
1552-4981
1552-4981
DOI:10.1002/jbm.b.31430