Y. Hwang, Chiou-Ping Hwang, R. Tsiang
Mar 14, 2003
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Journal
Journal of Applied Polymer Science
Abstract
Ethoxyethyl -cyanoacrylate was synthe- sized by first making oligo(ethoxyethyl -cyanoacrylate) through a condensation reaction of ethoxyethyl cyanoac- etate with paraformaldehyde, followed by a depolymeriza- tion of the oligomer at an elevated temperature in an acidic atmosphere with a high vacuum. The ethoxyethyl cyanoac- etate was in turn synthesized from an esterification of ethoxyethanol and cyanoacetic acid. The molecular structure of the target monomer and the corresponding intermediates were corroborated by IR and 1 H-NMR. Solvents having a lower polarity led to the formation of oligomers having higher molecular weights. The molecular weight distribu- tion of the oligomer revealed that the reaction of ethoxyethyl cyanoacetate with formaldehyde followed a mechanism comprising monomer activations, anionic reactions, and chain scissions. DSC thermograms demonstrated the cured ethoxyethyl -cyanoacrylate was nearly amorphous, con- taining little or low crystallinity. Mechanical testing data indicated that the cured ethoxyethyl -cyanoacrylate was a hard adhesive with higher toughness than the conventional ethyl -cyanoacrylate. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 87: 1758 -1773, 2003