Fatty acid derived renewable polyamidesviathiol–ene additions

Abstract

The syntheses of new fatty acid-derived amine functional monomers via the thiol–ene addition reaction as well as the thereof derived renewable polyamides were investigated. The thiol–ene addition of cysteamine hydrochloride to the double bonds of methyl 10-undecenoate, methyl oleate, and methyl erucate yielded heterodifunctional monomers in good yields. The thus obtained monomers were homopolymerized, copolymerized with each other as well as copolymerized with adipic acid and 1,6-hexamethylene diamine to yield copolyamides. 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) was used as an efficient amidation catalyst for all these polymerizations. GPC and DSC characterization of the polymers revealed that the renewable monomers can be used to produce polyamides with good properties and copolyamides with adjustable thermal and solubility properties.