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Peer-reviewedCC BYChemSusChem

Selective Chain Scission of L‐Lactide/ε‐Caprolactone Chain Shuttled Copolymers

  • A Noon1
  • L Fichaux1
  • X Mosca1
  • P A Lowy1
  • T Bousquet1
  • L Pelinski1
  • F Bonnet2
  • J P P Ramalho3
  • A Favrelle-Huret1
  • P Zinck1
  1. 1UCCS - Unité de Catalyse et Chimie du Solide (UMR 8181), Univ. Lille, CNRS, Centrale Lille, Univ. Artois, Villeneuve d'Ascq, France.
  2. 2UMET - Unité Matériaux et Transformations (UMR 8207), Univ. Lille, CNRS, INRAE, Centrale Lille, Lille, France.
  3. 3Chemistry and Biochemistry Department, Hercules Centre, Sciences and Technology School, University of Évora, Évora, Portugal.
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Abstract

In this work, we investigated selective strategies for the degradation of L-lactide/ε-caprolactone chain shuttled multiblock copolymers composed of PLLA-rich hard blocks and poly(ε-caprolactone-co-L-lactide) soft blocks. Enzymatic hydrolysis using the selective lipase from Pseudomonas cepacia, initially performed in aqueous buffer systems and subsequently in the presence of organic cosolvents, showed limited efficiency, likely due to limited enzymatic accessibility within the complex multiblock architecture. In contrast, homogeneous organocatalytic approaches showed higher degradation efficiency and selectivity. Base-catalyzed transesterification using 4-dimethylaminopyridine (DMAP) and imidazole enabled 100% selective chain scission toward lactyl units. Brønsted acid catalysis with p-toluenesulfonic acid (pTSA) and diphenyl phosphate (DPP) exhibited complementary transesterification selectivity, favoring degradation of caprolactoyl units and thus targeting the soft segments. The latter selectivity is particularly interesting, as it provides structural information about the chain-shuttled copolymers and allows to envision recycling of the PLA part. It is corroborated by DFT studies.

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Cite

BibTeXRIS
BibTeX
@article{noon2026selective,
  title = {{Selective Chain Scission of L‐Lactide/ε‐Caprolactone Chain Shuttled Copolymers}},
  author = {A Noon and L Fichaux and X Mosca and P A Lowy and T Bousquet and L Pelinski and F Bonnet and J P P Ramalho and A Favrelle-Huret and P Zinck},
  journal = {ChemSusChem},
  year = {2026},
  month = oct,
  doi = {10.1002/cssc.71174},
  url = {https://europepmc.org/article/PMC/PMC13722158},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Selective Chain Scission of L‐Lactide/ε‐Caprolactone Chain Shuttled Copolymers
AU  - A Noon
AU  - L Fichaux
AU  - X Mosca
AU  - P A Lowy
AU  - T Bousquet
AU  - L Pelinski
AU  - F Bonnet
AU  - J P P Ramalho
AU  - A Favrelle-Huret
AU  - P Zinck
PY  - 2026
DA  - 2026/10/30
JO  - ChemSusChem
DO  - 10.1002/cssc.71174
UR  - https://europepmc.org/article/PMC/PMC13722158
AB  - In this work, we investigated selective strategies for the degradation of L-lactide/ε-caprolactone chain shuttled multiblock copolymers composed of PLLA-rich hard blocks and poly(ε-caprolactone-co-L-lactide) soft blocks. Enzymatic hydrolysis using the selective lipase from Pseudomonas cepacia, initially performed in aqueous buffer systems and subsequently in the presence of organic cosolvents, showed limited efficiency, likely due to limited enzymatic accessibility within the complex multiblock architecture. In contrast, homogeneous organocatalytic approaches showed higher degradation efficiency and selectivity. Base-catalyzed transesterification using 4-dimethylaminopyridine (DMAP) and imidazole enabled 100% selective chain scission toward lactyl units. Brønsted acid catalysis with p-toluenesulfonic acid (pTSA) and diphenyl phosphate (DPP) exhibited complementary transesterification selectivity, favoring degradation of caprolactoyl units and thus targeting the soft segments. The latter selectivity is particularly interesting, as it provides structural information about the chain-shuttled copolymers and allows to envision recycling of the PLA part. It is corroborated by DFT studies.
SN  - 1864-5631
SN  - 1864-564X
ER  -