Preparation, Characterization, and Copolymerization of the 12-Membered Cyclic Diamide 1,6-Diazacyclododecane-2,5-dione
Document Type
Article
Publication Date
1-1-2014
Department
Polymers and High Performance Materials
Abstract
A 12-membered cyclic diamide monomer for nylon 64 was successfully synthesized in fairly high yield (approximate to 45%). The synthesis conditions were varied to see the effect of the diamine and succinyl chloride reactants on yield. Threefold excess of 1,6-hexamethylenediamine (HDA) gave the highest yield, while further increasing the amount of HDA decreased the yield. Using N,N-diisopropylethylamine as acid scavenger resulted in the formation of two different cyclic amides, which were fully analyzed by H-1 and C-13 solution nuclear magnetic resonance spectrometry and mass spectrometry. Copolymerization of cyclic amides with epsilon-caprolactam via an anionic route gave a block copolyamide with a two distinct endotherms in the differential scanning calorimetry analysis. However, copolymerization by the hydrolytic route gave only nylon 6 with terminal 64 units. (c) 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 96-103
Publication Title
Journal of Polymer Science Part A: Polymer Chemistry
Volume
52
Issue
1
First Page
96
Last Page
103
Recommended Citation
Kaya, E.,
Tarkin-Tas, E.,
Osborn, S.,
Ayotte, R.,
Manning, S. C.,
Mathias, L. J.
(2014). Preparation, Characterization, and Copolymerization of the 12-Membered Cyclic Diamide 1,6-Diazacyclododecane-2,5-dione. Journal of Polymer Science Part A: Polymer Chemistry, 52(1), 96-103.
Available at: https://aquila.usm.edu/fac_pubs/7931