Oligomeric epoxide-amine adducts based on 2-amino-N-isopropylacetamide and α-amino-ε-caprolactam: Solubility in presence of cyclodextrin and curing properties

Julian Fischer; Helmut Ritter

doi:10.3762/bjoc.9.315

Oligomeric epoxide-amine adducts based on 2-amino-N-isopropylacetamide and α-amino-ε-caprolactam: Solubility in presence of cyclodextrin and curing properties

Beilstein J Org Chem. 2013 Dec 5:9:2803-11. doi: 10.3762/bjoc.9.315. eCollection 2013.

Authors

Julian Fischer¹, Helmut Ritter¹

Affiliation

¹ Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf, Germany.

Abstract

2-Amino-N-isopropylacetamide and α-amino-ε-caprolactam were reacted with glycerol diglycidyl ether to give novel oligomeric thermoresponsive epoxide-amine adducts. These oligomers exhibit a lower critical solution temperature (LCST) behavior in water. The solubility properties were influenced with randomly methylated β-cyclodextrin (RAMEB-CD) and the curing properties of the amine-epoxide mixtures were analyzed by oscillatory rheology and differential scanning calorimetry, whereby significant differences in setting time, viscosity, and stiffness were observed.

Keywords: LCST; amino acids; curing properties; cyclodextrin; epoxide–amine oligomers.