MAISONNEUVE, Lise; WIROTIUS, Anne-Laure; ALFOS, Carine; GRAU, Etienne; CRAMAIL, Henri

doi:10.1039/c4py00922c

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MAISONNEUVE, Lise
Laboratoire de Chimie des Polymères Organiques [LCPO]

WIROTIUS, Anne-Laure
Laboratoire de Chimie des Polymères Organiques [LCPO]

ALFOS, Carine
Institut des Corps Gras [ITERG]

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Polymer Chemistry. 2014, vol. 5, n° 21, p. 6142-6147

Royal Society of Chemistry - RSC

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(Bis) 6-membered cyclic carbonates were prepared from methyl 10-undecenoate, which is produced from ricinoleic acid, a main constituent of castor oil. Kinetic studies on these new fatty acid-based 6-membered cyclic carbonates revealed that they are much more reactive than their homologs, 5-membered ones (30 times). Poly(hydroxyurethane)s (PHUs) were then synthesized from these bis 6-membered cyclic carbonates at a temperature as low as room temperature and in the solvent or bulk. Unexpectedly, chemical gels were obtained. The latter were the consequence of side reactions of carbonate ring-opening with the hydroxyl groups of the formed poly(hydroxyurethane)s. Quenching with a large excess of hexylamine enabled the breaking-up of the gel with the formation of urea linkages.< Leer menos

Palabras clave en inglés

1 3-DIOXAN-2-ONE

AMINE

SELECTIVITY

MONOMERS

REACTIVITY

POLYADDITION

POLYHYDROXYURETHANES

POLYURETHANES

MODEL REACTION

DIMETHYL CARBONATE

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Fatty acid-based (bis) 6-membered cyclic carbonates as efficient isocyanate free poly(hydroxyurethane) precursors

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