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Lipase‐Catalyzed Synthesis of Furan‐Based Oligoesters and their Self‐Assembly‐Assisted Polymerization
Author(s) -
Muthusamy Kumarasamy,
Lalitha Krishnamoorthy,
Prasad Yadavali Siva,
Thamizhanban Ayyapillai,
Sridharan Vellaisamy,
Maheswari C. Uma,
Nagarajan Subbiah
Publication year - 2018
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201800446
Subject(s) - monomer , candida antarctica , polymer chemistry , polymerization , polymer , gel permeation chromatography , differential scanning calorimetry , thermogravimetric analysis , molar mass distribution , chemistry , materials science , chemical engineering , organic chemistry , lipase , physics , engineering , thermodynamics , enzyme
We investigate the synthesis of bio‐based hydrophilic and hydrophobic oligoesters, which in turn are derived from easily accessible monomers from natural resources. In addition to the selection of renewable monomers, Novozyme 435, an immobilized lipase B from Candida antarctica was used for the oligomerization of monomers. The reaction conditions for oligomerization using Novozyme 435 were established to obtain a moderate‐to‐good yield. The average number of repeating units and the molecular weight distribution of hydrophilic and hydrophobic oligoester were identified by using NMR spectroscopy, gel‐permeation chromatography, and MS. The oligoester derived from a hydrophilic monomer self‐assembled to form a viscous solution, which upon further heating resulted in the formation of a polymer by the intermolecular Diels–Alder reaction. The viscosity of the solution and the assembly of oligoester to form a fibrous structure were investigated by using rheological studies, XRD, and SEM. The molecular weight of the cross‐linked polymer was identified by using matrix‐assisted laser desorption/ionization–MS. The thermal properties of the bio‐based polymers were investigated by using thermogravimetric analysis and differential scanning calorimetry. For the first time, the self‐assembly‐assisted polymerization of an oligoester is reported using the intermolecular Diels–Alder reaction, which opens a new avenue in the field of polymer science.