Facile Synthesis of Hydroxylated Dimethacrylates for Use in Biomedical Applications

Published

August 1, 2001

Author(s)

Michael Weir, C A. Khatri, Joseph M. Antonucci

Abstract

Novel hydroxylated dimethacrylates of various chemical structures were synthesized by reacting glycidyl methacrylate with an appropriate diacid to provide crosslinked polymers for biomedical applications. It is possible to tailor the chemico-physical and mechanical properties of the crosslinked network by changing the spacer group in the diacid. In this study, we synthesized a hydrophilic dimethacrylate based upon the diacid poly(ethylene glycol)-(bis(carboxymethyl) ether and a hydrophobic dimethacrylate based on dimer acid. NIR spectroscopy was effectively used to monitor the disappearance of the oxirane ring at 6070 cm^-1. Photopolymerization of the activated dimethacrylates occurred readily upon irradiation with visible light, with an extent of conversion {approximately equal to} 98 % (after 60 s), as determined by FT-IR spectroscopy. Additionally, dimer acid-GMA was copolymerized with Bis-GMA with an extent of conversion = 73 % (after 60 s). Crosslinking agents such as the PEG-diacid based dimethacrylate show promise in such applications as scaffolds for guided bone regeneration, where biodegradability is a key factor. By contrast, crosslinking agents such as the dimer acid based dimethacrylate may be useful as comonomers for the development of dental composites with enhanced biostability and toughness and low shrinkage and water adsorption.

Proceedings Title

ACS Meeting--to be published in Polymer Preprints

Volume

42(2)

Conference Dates

August 1, 2001

Conference Title

Polymer Preprints

Pub Type

Conferences

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Keywords

biomaterials, conversion, crosslinking, hydrophilic, hydrophobic, network, polymerization, synthesis

Citation

Weir, M. , Khatri, C. and Antonucci, J. (2001), Facile Synthesis of Hydroxylated Dimethacrylates for Use in Biomedical Applications, ACS Meeting--to be published in Polymer Preprints, [online], https://tsapps.nist.gov/publication/get_pdf.cfm?pub_id=851875 (Accessed April 24, 2024)