Lipase-catalyzed synthesis of acid-degradable poly(β-thioether ester) and poly(β-thioether ester-co-lactone) copolymers

A novel linear polyester with acid-labile beta -thiopropionate groups was synthesized via the direct lipase-catalyzed polycondensation of methyl 3-((2-hydroxyethyl)thio)propanoate (MHETP) using immobilized lipase B from Candida antarctica (CALB). The influences of reaction conditions such as polymer...

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Bibliographic Details
Published in:Polymer (Guilford) 2015-02, Vol.59, p.187-193
Main Authors: Wu, Wan-Xia, Qu, Lin, Liu, Bei-Yu, Zhang, Wei-Wei, Wang, Na, Yu, Xiao-Qi
Format: Article
Language:English
Subjects:
Candida antarctica
Copolymerization
Copolymers
Differential scanning calorimetry
Esters
Molecular weight
NMR spectroscopy
Nuclear magnetic resonance
Synthesis
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Summary:A novel linear polyester with acid-labile beta -thiopropionate groups was synthesized via the direct lipase-catalyzed polycondensation of methyl 3-((2-hydroxyethyl)thio)propanoate (MHETP) using immobilized lipase B from Candida antarctica (CALB). The influences of reaction conditions such as polymerization temperature and time on the molecular weight of the poly( beta -thioether ester) (PTE) were studied. Ring-opening and condensation copolymerization of MHETP with epsilon -caprolactone (CL) led to the synthesis of novel poly( beta -thioether ester-co- epsilon -caprolactone) copolymers, poly(TE-co-CL), with well-defined composition and narrow polydispersity. The random copolymers were characterized by 1H NMR, 13C NMR, 2D NMR, GPC, TGA and DSC. The degradation of the poly( beta -thioether ester) under acidic conditions was investigated by GPC and 1H NMR spectroscopy.
ISSN:0032-3861
DOI:10.1016/j.polymer.2015.01.002