Lipase-catalyzed synthesis of renewable acid-degradable poly(β-thioether ester) and poly(β-thioether ester-co-ricinoleic acid) copolymers derived from castor oil

• Published in: European polymer journal Vol. 121; p. 109315
• Main Authors: Wu, Wan-Xia, Li, Jun, Yang, Xian-Ling, Wang, Na, Yu, Xiao-Qi
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.12.2019; Elsevier BV
• Subjects: Acid-degradable; Castor oil; Chemical synthesis; Copolymerization; Copolymers; Enzymatic polymerization; Lipase; Molecular weight; NMR; Nuclear magnetic resonance; Organic chemistry; Poly(β-thioether ester); Polydispersity; Polymerization; Polymers; Renewable; Ricinoleic acid; Studies; Enzymatic polymerization; Renewable; Poly(β-thioether ester); Castor oil; Acid-degradable
• ISSN: 0014-3057; 1873-1945
• DOI: 10.1016/j.eurpolymj.2019.109315

[Display omitted] •Enzyme -catalyzed synthesis of renewable poly(β -thioether ester) for the first time.•Poly(UTE-co-RA) copolymers have tunable bifunctional groups.•PUTE and poly(UTE-co-RA) copolymers can be rapidly degraded under acidic condition. High-molecular-weight renewable semicrystalline poly(β-thioether ester) with acid-labile β-thiopropionate groups was synthesized via Candida antarctica lipase B (CALB)-catalyzed polycondensation of methyl 3-((11-hydroxyundecyl)thio)propanoate (MHUTP) derived from castor oil. The monmer was obtained through thiol-ene click chemistry. The influences of polymerization conditions such as reaction temperature and time on the molecular weight were studied. Copolymerization of MHUTP with methyl ricinoleate (MRA), another castor oil-derived renewable monmer, led to the synthesis of novel bifunctional poly(β-thioether ester-co-ricinoleic acid), poly(UTE-co-RA), copolymers with well-defined composition and narrow polydispersity. The homopolymers and random copolymers were characterized by NMR, GPC, TGA, DSC and WAXD. The degradation rate of the polymers under acidic conditions was investigated.