Synthesis of Self-Healing Supramolecular Rubbers from Fatty Acid Derivatives, DiethyleneTriamine, and Urea

We describe the synthesis of supramolecular self-healing elastomers from vegetable oil fatty acid derivatives, diethylene triamine, and urea. Our strategy to obtain materials that are self-healing but do not flow relies on the use of a wide molecular distribution of randomly branched oligomers equipped with self-complementary and complementary hydrogen bonding groups. We prepared such oligomers with a two steps procedure. In the first step, diethylene triamine was condensed with dimer acids. In the second step, the oligomers obtained were allowed to react with urea. The molecules were characterized by NMR and IR spectroscopies and Monte-Carlo simulations were used to analyze the molecular size distribution. The sensitivity to small variations of the experimental conditions has been examined and the robustness of the synthetic procedure optimized. (C) 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 7925-7936, 2008