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New biosourced alternated poly(ether)Ester-Amides (PeEA): synthesis and combined NMR/MALDI ToF MS characterization

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Abstract

New biosourced alternated poly(ether)Ester-Amides PeEA were prepared by polycondensation in solution or in bulk of unprecedented aminoalcohols based on 1,4:3,6-dianhydrohexitols (DAH) with aromatic and aliphatic diacyl chlorides (sebacoyl, terephtaloyl and isophtaloyl). Optimization of the polymerization in solution has been investigated using MALDI ToF MS and NMR spectroscopy to ascertain the structures and end chain nature of the resulting polymers. The influence of the DAH stereochemistry and the polymerization mode on the structures and thermal properties was demonstrated by MALDI ToF and complementary analytical techniques (DSC and SEC). Isomannide based polymers revealed amorphous but showed higher Tg (around 80 °C for sebacoyl and 180 °C for isophtaloyl) whereas the isosorbide based polymers were semi crystalline. Best properties were obtained in bulk using isomannide based aminoalcohol and sebacoyl chloride (Tg of 82 °C and Mw of 32 kDa, PDI = 1.41).

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Acknowledgments

Authors are grateful to Société Roquette Lestrem for a kind gift of Isosorbide and Isomannide. The authors want to thank the Tunisian Ministry of Higher Education and Research and the French Foreign affairs Ministry for Financial support (Project “PHC Utique” 13G/1211). Authors want to thanks all INRAP staff especially (Mr Chaouki Belgacem and Mohamed Mezni, Mrs Saloua Ben Aissa and Monia Elouni) for analysis and helpful discussions.

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Authors and Affiliations

  1. Laboratoire des Substances Naturelles (LSN), LR10 INRAP 02, Institut National de Recherche et d’Analyse Physico-chimique INRAP, Sidi Thabet Biotechpole, 2020, Ariana, Tunisia

    Raouf Medimagh, Asma Saadaoui & Salma Mghirbi

  2. Université de Versailles-St-Quentin (UVSQ), Institut Lavoisier de Versailles (ILV) UMR CNRS 8180, 45 Avenue des Etats-Unis, 78035, Versailles Cedex, France

    Asma Saadaoui, Sylvain Marque & Damien Prim

  3. Université de Lyon, UMR 5280, Institut des Sciences Analytiques (ISA), 5 rue de la Doua, 69100, Villeurbanne, France

    Aurélie Fildier, Audrey Bulete, Guy Raffin & Saber Chatti

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  1. Raouf Medimagh
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  2. Asma Saadaoui
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  3. Salma Mghirbi
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  4. Sylvain Marque
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  9. Saber Chatti
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Correspondence to Raouf Medimagh or Saber Chatti.

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Medimagh, R., Saadaoui, A., Mghirbi, S. et al. New biosourced alternated poly(ether)Ester-Amides (PeEA): synthesis and combined NMR/MALDI ToF MS characterization. J Polym Res 21, 486 (2014). https://doi.org/10.1007/s10965-014-0486-4

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