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Article Dans Une Revue Polymer Chemistry Année : 2012

Cationic polyesters bearing pendent amino groups prepared by thiol-ene chemistry.

Résumé

A straightforward approach based on thiol-ene click chemistry was used to prepare novel functional polyesters containing amino groups. First, a series of well-defined alkene-functional poly(ε-caprolactone)s were prepared by ring-opening polymerization of α-allyl-ε-caprolactone with ε-caprolactone in toluene and in bulk using tin 2-ethylhexanoate as catalyst. These functional polyesters were fully characterized by 1H NMR, GPC, and MALDI-TOF MS. The resulting random copolyesters were obtained with a wide range of molar masses from 3000 to 50[thin space (1/6-em)]000 g mol−1 and a good incorporation of the α-allyl-ε-caprolactone monomer unit. Then, thiol-ene reaction of alkene-functional PCL with the 2-(Boc-amino)ethanethiol was used to prepare efficiently polyesters bearing protected amino groups without chain degradation. Finally, cationic and water-soluble polyesters bearing free amino groups were recovered by cleavage of the Boc protecting group. These aminated polyesters were characterized by 1H NMR in deuterated water.

Domaines

Chimie organique
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Dates et versions

hal-00672344 , version 1 (21-02-2012)

Identifiants

Citer

Vincent Darcos, S. Antoniacomi, Cédric Paniagua, Jean Coudane. Cationic polyesters bearing pendent amino groups prepared by thiol-ene chemistry.. Polymer Chemistry, 2012, 3, pp.362-368. ⟨10.1039/c1py00414j⟩. ⟨hal-00672344⟩
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