Biobased cross-linked polyurethanes obtained from ester/amide pseudo-diols of fatty acid derivatives synthesized by thiol-ene coupling - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Polymer Chemistry Année : 2011

Biobased cross-linked polyurethanes obtained from ester/amide pseudo-diols of fatty acid derivatives synthesized by thiol-ene coupling

Résumé

Ester-containing pseudo-telechelic diols of fatty acid derivatives were synthesized via a two-step reaction (transesterification with diol compounds followed by thiol-ene radical coupling), and amidecontaining pseudo-telechelic diols of fatty acid derivatives were also synthesized in a similar way, i.e. amidification reaction followed by thiol-ene radical coupling. A wide range of both ester- and amidecontaining pseudo-telechelic diols were thus obtained by varying the spacer length between either ester or amide functions. These compounds were thoroughly characterized by means of NMR analysis and by titration. Their viscosity as well as their thermal behavior was assessed. Polyurethanes (PUs) were then obtained by reaction with a commercially available diisocyanate (MDI prepolymer). It was shown that thermostability of PUs was higher when using ester-containing pseudo-telechelic diols. In contrast, the amide groups increase the glass transition temperature of PUs through hydrogen bonding and also accelerate the network formation by acting as catalyst. Finally we showed that the higher the chain length in between functional groups the higher the softness of the PUs.

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Polymères
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Dates et versions

hal-00726056 , version 1 (28-08-2012)

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Myriam Desroches, Sylvain Caillol, Rémi Auvergne, Bernard Boutevin, Ghislain David. Biobased cross-linked polyurethanes obtained from ester/amide pseudo-diols of fatty acid derivatives synthesized by thiol-ene coupling. Polymer Chemistry, 2011, 3, pp.450. ⟨10.1039/c1py00479d⟩. ⟨hal-00726056⟩
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