The current ocean trash crisis, added to non-guaranteed availability of oil and natural gas in the future, denotes the need for alternatives to current commodity plastics. The design of novel polymers should include the utilization of renewable resources for monomer preparation, as well as the installation of chemically cleavable groups to guarantee their degradation. We have chosen polyaldimines as suitable polymer systems to fulfill those premises. The aldimine functionality is present in nature, and comes from the reaction of an aldehyde and an amine, releasing a molecule of water. We utilized aromatic aldehydes that can be obtained from the pyrolysis of lignin, of which vanillin is the best example. Aldehydes were linked via ethylene to yield dialdehydes, and then combined with commercially available diamines. The diamines were aliphatic with 2-6 methylene spacers. Although these diamines are not currently sustainable, they could be prepared from renewable α-ω diols and ammonia. Obtained polymers had adequate thermal properties to compete with commodity plastics, with Tg ranging from 58 to 165 °C, and some of the samples were crystalline with Tm ranging from 143 to 297 °C. Preliminary degradation studies showed polymers start hydrolyzing immediately after exposure to acidic buffers in heterogeneous conditions.

Sustainable polyaldimines from lignin-derived aromatic aldehydes and aliphatic diamines

253rd National Meeting (2017)

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