Synthesis of Network Biobased Aliphatic Polyesters Exhibiting Better Tensile Properties than the Linear Polymers by ADMET Polymerization in the Presence of Glycerol Tris(undec-10-enoate)

Go, Lance O’Hari P.; Abdellatif, Mohamed Mehawed; Makino, Ryoji; Shimoyama, Daisuke; Higashi, Seiji; Hirano, Hiroshi; Nomura, Kotohiro

doi:10.3390/polym16040468

Open AccessArticle

Synthesis of Network Biobased Aliphatic Polyesters Exhibiting Better Tensile Properties than the Linear Polymers by ADMET Polymerization in the Presence of Glycerol Tris(undec-10-enoate)

by

Lance O’Hari P. Go

¹

,

Mohamed Mehawed Abdellatif

¹,

Ryoji Makino

¹,

Daisuke Shimoyama

¹,

Seiji Higashi

²,

Hiroshi Hirano

²

and

Kotohiro Nomura

^1,*

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

^*

Author to whom correspondence should be addressed.

Polymers 2024, 16(4), 468; https://doi.org/10.3390/polym16040468

Submission received: 30 December 2023 / Revised: 27 January 2024 / Accepted: 5 February 2024 / Published: 7 February 2024

(This article belongs to the Special Issue Catalytic Olefin Polymerization and Polyolefin Materials)

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Abstract

Development of biobased aliphatic polyesters with better mechanical (tensile) properties in film has attracted considerable attention. This report presents the synthesis of soluble network biobased aliphatic polyesters by acyclic diene metathesis (ADMET) polymerization of bis(undec-10-enyl)isosorbide diester [M1, dianhydro-D-glucityl bis(undec-10-enoate)] in the presence of a tri-arm crosslinker [CL, glycerol tris(undec-10-enoate)] using a ruthenium–carbene catalyst, and subsequent olefin hydrogenation using RhCl(PPh₃)₃. The resultant polymers, after hydrogenation (expressed as HCP1) and prepared in the presence of 1.0 mol% CL, showed better tensile properties than the linear polymer (HP1) with similar molecular weight [tensile strength (elongation at break): 20.8 MPa (282%) in HP1 vs. 35.4 MPa (572%) in HCP1]. It turned out that the polymer films prepared by the addition of CL during the polymerization (expressed as a 2-step approach) showed better tensile properties. The resultant polymer film also shows better tensile properties than the conventional polyolefins such as linear high density polyethylene, polypropylene, and low density polyethylene.

Keywords: olefin metathesis; polymerization; biobased; isosorbide; polyesters; network; tensile property; chemical recycling

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MDPI and ACS Style

Go, L.O.P.; Abdellatif, M.M.; Makino, R.; Shimoyama, D.; Higashi, S.; Hirano, H.; Nomura, K. Synthesis of Network Biobased Aliphatic Polyesters Exhibiting Better Tensile Properties than the Linear Polymers by ADMET Polymerization in the Presence of Glycerol Tris(undec-10-enoate). Polymers 2024, 16, 468. https://doi.org/10.3390/polym16040468

AMA Style

Go LOP, Abdellatif MM, Makino R, Shimoyama D, Higashi S, Hirano H, Nomura K. Synthesis of Network Biobased Aliphatic Polyesters Exhibiting Better Tensile Properties than the Linear Polymers by ADMET Polymerization in the Presence of Glycerol Tris(undec-10-enoate). Polymers. 2024; 16(4):468. https://doi.org/10.3390/polym16040468

Chicago/Turabian Style

Go, Lance O’Hari P., Mohamed Mehawed Abdellatif, Ryoji Makino, Daisuke Shimoyama, Seiji Higashi, Hiroshi Hirano, and Kotohiro Nomura. 2024. "Synthesis of Network Biobased Aliphatic Polyesters Exhibiting Better Tensile Properties than the Linear Polymers by ADMET Polymerization in the Presence of Glycerol Tris(undec-10-enoate)" Polymers 16, no. 4: 468. https://doi.org/10.3390/polym16040468

APA Style

Go, L. O. P., Abdellatif, M. M., Makino, R., Shimoyama, D., Higashi, S., Hirano, H., & Nomura, K. (2024). Synthesis of Network Biobased Aliphatic Polyesters Exhibiting Better Tensile Properties than the Linear Polymers by ADMET Polymerization in the Presence of Glycerol Tris(undec-10-enoate). Polymers, 16(4), 468. https://doi.org/10.3390/polym16040468

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Synthesis of Network Biobased Aliphatic Polyesters Exhibiting Better Tensile Properties than the Linear Polymers by ADMET Polymerization in the Presence of Glycerol Tris(undec-10-enoate)

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