Issue 4, 2012
From the journal:

Polymer Chemistry

Imidazole-accelerated crosslinking of epoxidized natural rubber by dicarboxylic acids: a mechanistic investigation using NMR spectroscopy†

Myriam Pire,a   Cédric Lorthioir,b   Evdokia K. Oikonomou,a   Sophie Norvez,*a   Ilias Iliopoulos,a   Benoît Le Rossignolc  and  Ludwik Leiblera  

* Corresponding authors

a Matière Molle et Chimie, ESPCI ParisTech—CNRS, UMR-7167, 10 rue Vauquelin, Paris, France
E-mail: sophie.norvez@espci.fr
Fax: +33 140-795-117
Tel: +33 140-795-113

b Institut de Chimie et des Matériaux Paris-Est, UMR-7182 CNRS—UPEC, 2-8 rue Henri Dunant, Thiais, France

c Hutchinson SA Centre de Recherche, rue Gustave Nourry, BP31, Châlette sur Loing Cedex, France

Abstract

The crosslinking of epoxidized natural rubber with dodecanedioic acid and the mechanism of its acceleration by 1,2-dimethylimidazole (DMI) are investigated using nuclear magnetic resonance spectroscopy. Solid-state NMR experiments (1H, 1H → 13C cross-polarization and 13C direct polarization) are used to analyse crosslinked samples, whereas 13C solution NMR provides information about liquid epoxidized rubber species. 13C solid-state NMR demonstrates the ester nature of the crosslinks, and confirms that DMI acts through the formation of imidazolium dicarboxylate species, well dispersed in the elastomeric matrix. After synthesis of a low molecular weight epoxidized rubber and subsequent reaction with a monofunctional carboxylic acid in the presence of DMI, a solution NMR study reveals that the imidazolium dicarboxylate would react preferentially at the less substituted side of the epoxy site.

Graphical abstract: Imidazole-accelerated crosslinking of epoxidized natural rubber by dicarboxylic acids: a mechanistic investigation using NMR spectroscopy

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Article information

DOI
https://doi.org/10.1039/C2PY00591C
Article type
Paper
Submitted
15 Dec 2011
Accepted
11 Jan 2012
First published
31 Jan 2012

Polym. Chem., 2012,3, 946-953

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Imidazole-accelerated crosslinking of epoxidized natural rubber by dicarboxylic acids: a mechanistic investigation using NMR spectroscopy

M. Pire, C. Lorthioir, E. K. Oikonomou, S. Norvez, I. Iliopoulos, B. Le Rossignol and L. Leibler, Polym. Chem., 2012, 3, 946 DOI: 10.1039/C2PY00591C

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