Issue 15, 2024

Bio-based, random terpolymers with defined functionality based on poly(limonene carbonate-ran-menth-1-ene carbonate)

Abstract

The increasing shortage in fossil resources creates a strong demand for the development of bio-based polymers with tailored properties, not competing with food resources. Polycarbonates, produced by ring-opening copolymerization (ROCOP) of epoxides and CO2, are one promising material class to solve this issue. Poly(limonene carbonate) (PLimC) is a bio-based and non-food based polycarbonate made from limonene oxide (LimO) and CO2. It features an exocyclic double bond at each repeating unit, which can be utilized for further functionalization reactions. However, the degree of functionalization is hardly controllable. Here, we demonstrate that random terpolymerization of LimO with its hydrogenated analogue menth-1-ene oxide (Men1O) and CO2 gives access to polycarbonates with a defined number and homogeneous distribution of functional groups within the polymer chain. The reactivity ratios, determined by the Fineman-Ross and non-linear least square (NLLS) methods, are close to 1.0 for both LimO and Men1O, proving the random nature of the terpolymerization. The versatility of this synthetic platform is shown by thiol–ene click functionalization with 2-mercaptoethanol, yielding terpolymers with a defined number of pendant hydroxy groups. These are exemplarily used for fluorescence labelling of solution cast films with 5-fluorescein isothiocyanate (FITC), revealing a high accessibility of the pendant hydroxy groups for further reactions, even in heterogeneous systems.

Graphical abstract: Bio-based, random terpolymers with defined functionality based on poly(limonene carbonate-ran-menth-1-ene carbonate)

Supplementary files

Article information

Article type
Paper
Submitted
04 Dec 2023
Accepted
29 Feb 2024
First published
01 Mar 2024
This article is Open Access
Creative Commons BY license

Polym. Chem., 2024,15, 1522-1529

Bio-based, random terpolymers with defined functionality based on poly(limonene carbonate-ran-menth-1-ene carbonate)

M. Höferth, H. Schmalz and A. Greiner, Polym. Chem., 2024, 15, 1522 DOI: 10.1039/D3PY01331F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements