Synthesis of High Molecular Weight Biobased Aliphatic Polyesters Exhibiting Tensile Properties Beyond Polyethylene

Mika Kojima; Xiuxiu Wang; Lance O'Hari P Go; Ryoji Makino; Yuichi Matsumoto; Daisuke Shimoyama; Mohamed Mehawed Abdellatif; Joji Kadota; Seiji Higashi; Hiroshi Hirano; Kotohiro Nomura

doi:10.1021/acsmacrolett.3c00481

Synthesis of High Molecular Weight Biobased Aliphatic Polyesters Exhibiting Tensile Properties Beyond Polyethylene

ACS Macro Lett. 2023 Oct 17;12(10):1403-1408. doi: 10.1021/acsmacrolett.3c00481. Epub 2023 Oct 4.

Affiliations

¹ Department of Chemistry, Tokyo Metropolitan University, 1-1 minami Osawa, Hachioji, Tokyo 192-0397, Japan.
² Osaka Research Institute of Industrial Science and Technology (ORIST), 1-6-50, Morinomiya, Joto-ku, Osaka 536-8553, Japan.

Abstract

Synthesis of high molecular weight polyesters prepared by acyclic diene metathesis (ADMET) polymerization of bis(undec-10-enoate) with isosorbide (M1), isomannide (M2), and 1,3-propanediol (M3) and the subsequent hydrogenation have been achieved by using a molybdenum-alkylidene catalyst. The resultant polymers (P1) prepared by the ADMET polymerization of M1 (in toluene at 25 °C) possessed high M_n values (M_n = 44400-49400 g/mol), and no significant differences in the M_n values and the PDI (M_w/M_n) values were observed in the samples after the hydrogenation. Both the tensile strength and the elongation at break in the hydrogenated polymers from M1 (HP1) increased upon increasing the molar mass, and the sample with an M_n value of 48200 exhibited better tensile properties (tensile strength of 39.7 MPa, elongation at break of 436%) than conventional polyethylene, polypropylene, as well as polyester containing C₁₈ alkyl chains. The tensile properties were affected by the diol segment employed, whereas HP2 showed a similar property to HP1.