Novel green fatty acid-based bis-cyclic carbonates for the synthesis of isocyanate-free poly(hydroxyurethane amide)s

Lise Maisonneuve; Arvind S. More; Stéphanie Foltran; Carine Alfos; Fréderic Robert; Yannick Landais; Thierry Tassaing; Etienne Grau; Henri Cramail

doi:10.1039/C4RA03675A

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Novel green fatty acid-based bis-cyclic carbonates for the synthesis of isocyanate-free poly(hydroxyurethane amide)s†

Lise Maisonneuve,^ab Arvind S. More,^ab Stéphanie Foltran,^cd Carine Alfos,^e Fréderic Robert,^cd Yannick Landais,^cd Thierry Tassaing,^cd Etienne Grau^ab and Henri Cramail*^ab

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* Corresponding authors

^a Centre National de la Recherche Scientifique, Laboratoire de Chimie des Polymères Organiques, UMR 5629, IPB/ENSCBP, 16 avenue Pey-Berland, F-33607 Pessac Cedex, France
E-mail: cramail@enscbp.fr

^b Univ. of Bordeaux, Laboratoire de Chimie des Polymères Organiques, UMR 5629, IPB/ENSCBP, 16 avenue Pey-Berland, F-33607 Pessac Cedex, France

^c Centre National de la Recherche Scientifique, Institut des Sciences Moléculaires, UMR 5255, 351, Cours de la libération, 33405 Talence Cedex, France

^d Univ. of Bordeaux, Institut des Sciences Moléculaires, UMR 5255, 351, Cours de la libération, 33405 Talence Cedex, France

^e ITERG, 11 rue Gaspard Monge, F-33600 Pessac Cedex, France

Abstract

Fatty acid-based bis-cyclic 5-membered carbonates containing amide linkages were prepared from methyl 10-undecenoate. The reaction in bulk of these bio-based carbonates with a series of di-amines led to poly(hydroxyurethane amide)s with molar masses up to 31 000 g mol⁻¹. As expected, the so-formed bio-based thermoplastic poly(hydroxyurethane)s exhibit amorphous to semi-crystalline features with respect to the chemical structure of the monomers used.

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DOI: https://doi.org/10.1039/C4RA03675A
Article type: Paper
Submitted: 22 Apr 2014
Accepted: 03 Jun 2014
First published: 03 Jun 2014

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RSC Adv., 2014,4, 25795-25803

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Novel green fatty acid-based bis-cyclic carbonates for the synthesis of isocyanate-free poly(hydroxyurethane amide)s

L. Maisonneuve, A. S. More, S. Foltran, C. Alfos, F. Robert, Y. Landais, T. Tassaing, E. Grau and H. Cramail, RSC Adv., 2014, 4, 25795 DOI: 10.1039/C4RA03675A

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Novel green fatty acid-based bis-cyclic carbonates for the synthesis of isocyanate-free poly(hydroxyurethane amide)s†

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