N,N'-(Hexane-1,6-diyl)bis(4-methyl-N-(oxiran-2-ylmethyl)benzenesulfonamide): Synthesis via cyclodextrin mediated N-alkylation in aqueous solution and further Prilezhaev epoxidation

• Julian Fischer,
• Simon Millan and
• Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 2834–2840, doi:10.3762/bjoc.9.318

• adequate phase transfer catalysts and the cyclodextrin–guest complexes were characterized by 1H NMR and 2D NMR ROESY spectroscopy. Finally, the curing properties of the diepoxide with lysine-based α-amino-ε-caprolactam were analyzed by rheological measurements. Keywords: alkylation; cyclodextrins; epoxy

• -2-ylmethyl)benzenesulfonamide) (6). The proceeding reaction was monitored by means of 1H NMR spectroscopy, since the allyl protons of 5 in the range of 5.0 to 5.7 ppm vanish on conversion (Figure S3, Supporting Information File 1). To illustrate the curing properties of the synthesized diepoxide, 6

• conversion. The resulting poly-adduct 9 exhibits a glass transition temperature (Tg) of around 49 °C. Equivalent measurements of standard BADGE demonstrated a gelpoint after about 99 min and a Tg of about 74 °C (Figure S4, Supporting Information File 1). Thus, the curing properties for a mixture of 6 with 8

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 and
• Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 2803–2811, doi:10.3762/bjoc.9.315

• 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: amino acids; curing properties; cyclodextrin; epoxide–amine oligomers; LCST; Introduction Many partially hydrophobic

• be shaped before curing and keeps this shape as a free-standing-disc after hardening (Figure 5d). This can be emphasized with the fact that G‘ and G‘‘ diverge considerably after the gel point transition. A direct comparison of the curing properties of 9 and 10 is given in Figure 4c, which displays