Polymerizable ring-shaped molecules containing aspartic acid: synthesis and free radical polymerization of a macrocycle derived from (N'-methacryloyl-11-aminoundecanoyl)-α,β-bis(4,9-dioxa-dodecane-1,12-diamine)-L-aspartic acid amide by addition to toluene-2,4-diisocyanate

Abstract

A novel polymerizable macrocycle, 6, was prepared using high dilution techniques. Starting from N-(N'-methacryloyl-11-aminoundecanoyl)-L-aspartic acid dimethyl ester (2), N-(N'methacryloyl-11-aminoundecanoyl)-α,β-bis( 4,9-dioxadodecane-1,12-diamine)-L-aspartic acid amide (4) was obtained via amino-lysis with the bifunctional amine 4,9-dioxadodecane-1,12-diamine (3) in high excess. Addition of the free amino groups to toluene-2,4-diisocyanate (5) under high dilution provided macrocycle 6. The existence and purity of 6 were confirmed by mass spectrometry, NMR and IR spectroscopy, and HPLC. The methacrylic function was used to build up oligomers by free radical polymerization, using AIBN as an initiator.