From Forest to Future: Synthesis of Sustainable High Molecular Weight Polyamides Using and Investigating the AROP of β-Pinene Lactam

Macromol Rapid Commun. 2024 Feb;45(3):e2300524. doi: 10.1002/marc.202300524. Epub 2023 Nov 27.

Abstract

Polyamides (PA) are among the most essential and versatile polymers due to their outstanding characteristics, for example, high chemical resistance and temperature stability. Furthermore, nature-derived monomers can introduce hard-to-synthesize structures into the PAs for unique polymer properties. Pinene, as one of the most abundant terpenes in nature and its presumable stability-giving bicyclic structure, is therefore highly promising. This work presents simple anionic ring-opening polymerizations of β-pinene lactam (AROP) in-bulk and in solution. PAs with high molecular weights, suitable for further processing, are produced. Their good mechanical, thermal (Td s up to 440 °C), and transparent appearance render them promising high-performance biomaterials. In the following, the suitability of different initiators is discussed. Thereby, it is found that NaH is the most successful for in-bulk polymerization, with a degree of polymerization (DP) of about 322. For solution-AROP, iPrMgCl·LiCl is successfully used for the first time, achieving DPs up to about 163. The obtained PAs are also hot-pressed, and the dynamic mechanical properties are analyzed.

Keywords: anionic ring-opening polymerization; biopolyamide; dynamic mechanical analysis; solution polymerization; β-pinene-based polyamide.

MeSH terms

  • Bicyclic Monoterpenes*
  • Forests
  • Lactams* / chemistry
  • Molecular Weight
  • Nylons / chemistry
  • Polymerization
  • Polymers / chemistry
  • beta-Lactams*

Substances

  • Lactams
  • beta-Lactams
  • beta-pinene
  • Nylons
  • Polymers
  • Bicyclic Monoterpenes