Evaluation of alternative monomers to HEMA for dental applications.

Dent Mater

Ivoclar Vivadent AG, Bendererstrasse 2, FL-9494 Schaan, Liechtenstein.

Published: July 2017

Objective: The objective of this work is to find potential alternative monomers to 2-hydroxyethyl methacrylate (HEMA) for dental materials (self-etch adhesives and luting composites).

Methods: Monomers 1-9 were tested as potential HEMA substitutes. Methacrylates 4, 5 and 6 and (N-methyl)acrylamides 7-9 were synthesized and characterized by H NMR spectroscopy. The reactivity of each monomer was studied using photo-DSC. Mixtures of monomers 1-9 with the urethane dimethacrylate UDMA (1/1: wt/wt) were formulated and cured. The water sorption and solubility of these materials were determined according to ISO 4049. Luting composites based on monomers 1-9 or on HEMA were formulated. The flexural strength and modulus of elasticity were measured using a three-point bending setup, according to ISO 4049. Self-etch adhesives containing monomers 1-9 or HEMA were prepared and used to mediate a bond between the dental composite Tetric EvoCeram and both dentin and enamel. The shear bond strength (SBS) was measured using a Zwick universal testing machine.

Results: Polymerizable diols 3 and 4 as well as (N-methyl)acrylamides 7-9 were found to be significantly more reactive than HEMA. Resins based on the hydrophilic monomers 3, 7 and 8 exhibited a significantly higher water sorption than the corresponding HEMA-containing material. Luting composites containing monomers 2, 3, 6 and 7 showed similar or even improved mechanical properties compared to the reference material containing HEMA. Self-etch adhesives containing monomers 4 and 9 provided significantly higher dentin SBS than the reference material.

Significance: Some of the evaluated monomers are promising candidates for the development of HEMA-free dental materials.

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http://dx.doi.org/10.1016/j.dental.2017.04.023DOI Listing

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