An Improved Synthesis of Ethyl Alpha-Hydroxymethylacrylate, a Unique Isomeric Analog of HEMA

Published

August 1, 2000

Author(s)

Joseph M. Antonucci, J W. Stansbury, Bruce O. Fowler

Abstract

HEMA is widely used in dental adhesives, bioactive composites and resin-modified glass ionomer cements. In its polymeric forms it is used in a number of biomedical applications, e.g. hydrogels for controlled-release, soft contact lenses, vascular grafts and soft tissue. Poly (HEMA) was the first synthetic hydrogel intended for use as a biomaterial. A unique isomeric analog of HEMA, ethyl-α-hydroxymethyl acrylate (EHMA) was synthesized in the 1980's. In this study a new high yield preparation was developed. The synthetic method can be extended to the preparation of a variety of α-hydroxymethyl acrylates. Photopolymerization studies were performed to compare the rates and extents of polymerization of HEMA versus EHMA in homo- and co-polymer systems. While EHMA polymerized at a slower rate than HEMA, the final vinyl conversions values of these monomer were similar. Their copolymerizations with Bis-GMA gave similar rates and conversion values. Supported by NIST/NIDCR 1A Y1-DE7006-0.

Proceedings Title

American Chemical Society; Division of Polymer Chemistry, Meeting | | | American Chemical Society

Volume

41

Issue

No. 2

Conference Dates

August 20-24, 2000

Conference Location

Undefined

Conference Title

Polymer Preprints

Pub Type

Conferences

Download Paper

Local Download

Keywords

2-hydroxyethylmethacrylate, conversion, ethyl α-hydroxymethylacrylate, photopolymerization, sythesis, Dentistry

Citation

Antonucci, J. , Stansbury, J. and Fowler, B. (2000), An Improved Synthesis of Ethyl Alpha-Hydroxymethylacrylate, a Unique Isomeric Analog of HEMA, American Chemical Society; Division of Polymer Chemistry, Meeting | | | American Chemical Society, Undefined, [online], https://tsapps.nist.gov/publication/get_pdf.cfm?pub_id=851708 (Accessed October 27, 2025)