Abstract
In this work, four isohexide-derived isomeric dianhydrides were synthesized through a four-step procedure using isohexide and chloro-N-phenylphthalimides as the starting materials. The one-step solution polymerization of these dianhydrides with petroleum- or bio-based diamines enabled the synthesis of poly(ether imide)s (PEIs), which had viscosities of 0.41 to 2.40 dL∙g−1. The isohexide-derived PEIs were characterized based upon their solubility and their thermal, mechanical, and optical properties. The results showed that most of the isohexide-derived PEIs possessed comparable glass transition temperatures (Tg), tensile strengths, and moduli to petroleum-based PEIs. However, the thermo-oxidative stability of the PEIs was found to be lower than that of the common petroleum-based PEIs. Moreover, the PEIs displayed good optical activity, which originated from their unique chiral isohexide moieties. The isomeric effects of dianhydride monomers on the properties of the resulting PEIs were comparatively studied. The results suggested that the corresponding 4,4′-linked PEIs possessed lower Tg, higher mechanical properties, and higher specific rotations compared to 3,3′-linked polymers. Meanwhile, the polyimides with isomannide residue displayed higher Tg and more specific rotations than the corresponding polymers with isosorbide residue. These results contributed to more restricted rotations of phthalimide segments in 3,3′-linked or isomannide containing polyimides.
Highlights
Due to the depletion of petroleum reserves and the increase in ecological concerns caused by the production of vast amounts of non-degradable plastics, the development of polymers from renewable feedstocks has garnered considerable interest from both academia and industry [1,2,3].In this regard, 1,4:3,6-dianhydrohexitols have been considered a family of attractive bio-sourced monomers for the polymer industry, owing to their several inherent advantages
poly(ether imide)s (PEIs) based on DAII and DAIS exhibited relatively lower thermo-oxidative stability than their aromatic diamines (ODA, MDA, and m-PDA) based counterparts, which could be due to their higher alicyclic contents
Except for the PEIs based on 3,30 -ISDPA and aromatic diamines, all other isohexide-derived PEIs were dextrorotary, with the specific rotation values lying within the range of (+) 86◦ –(+) 370◦
Summary
Due to the depletion of petroleum reserves and the increase in ecological concerns caused by the production of vast amounts of non-degradable plastics, the development of polymers from renewable feedstocks has garnered considerable interest from both academia and industry [1,2,3]. The majority of dianhydride and diamine monomers, used for the synthesis of polyimides, are produced using petroleum-based chemicals as the raw materials. A series of bio-based polyimides were synthesized using diamino-isosorbide, diamino-isoidide, bis(4-aminophenyl) isosorbide, and bis(4-aminophenyl) isomannide These polyimides showed excellent optical transparency and optical activity, comparable thermal and mechanical properties to petroleum-based polyimides, and reasonably high bio-based contents [45,46]. Chen and coworkers reported the synthesis of bio-based dianhydride using isomannide and 4-nitrophthalonitrile as the raw materials and the preparation of isomannide-derived diamines through either direct substitution or chain extension reactions. A conventional two-step method has been used to prepare bio-based polyimides with good optical transparency and integrated properties using these isomannide-derived monomers [48]. The properties of synthesized bio-based PEIs were characterized in detail, and the isomeric effects of dianhydride monomers on the properties of the resulting polymers were systematically investigated
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