Investigation on the organocatalyzed ROP of δ-tetradecalactone: From polymerization to biodegradation - Archive ouverte HAL Access content directly
Journal Articles European Polymer Journal Year : 2024

Investigation on the organocatalyzed ROP of δ-tetradecalactone: From polymerization to biodegradation

Abstract

Searching for biobased and biodegradable polymers, we explored the organocatalytic ring-opening polymerization (ROP) of a renewable n-alkyl δ-lactone, namely δ-tetradecalactone (δ-TDL) that can be extracted from coconut oil, and we studied the ready biodegradability of the corresponding polyester. As reported for other nalkyl δ-lactones, 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) was used to perform the bulk and room temperature ROP of δ-TDL. A study of the purification of the monomer prior to its ROP showed the importance of the combination of a distillation process and an elution through basic alumina to remove most of the impurities and obtain the higher molar masses. Despite this careful purification, capped molar masses were obtained (<40 kg/ mol) and attributed by NMR and MALDI-ToF spectroscopy to TBD initiation and other side-initiators contained in the monomer, which were not possible to be identified. Other catalysts such as diphenyl phosphate (DPP) and the phosphazene superbase t-BuP 4 combined with a thiourea were also tried. The assessment of poly(δ-tetradecalactone) (pTDL) ready biodegradability was finally performed using the OECD test guideline 301F and showed the obtention of up to 41 % biodegradation rate in 28 days using a bioavailability improvement method.
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hal-04472323 , version 1 (22-02-2024)

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Attribution - NonCommercial - NoDerivatives

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Peter Mcmichael, Xavier Schultze, Henri Cramail, Frédéric Peruch. Investigation on the organocatalyzed ROP of δ-tetradecalactone: From polymerization to biodegradation. European Polymer Journal, 2024, 208, pp.112859. ⟨10.1016/j.eurpolymj.2024.112859⟩. ⟨hal-04472323⟩

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