Fully Bio-based Aromatic Polyimide Using 4-Aminocinnamic Acid and Mellophanic Dianhydride as Bio-derived Monomers

Abstract

Mellophanic dianhydride which is aromatic tetracarboxylic dianhydride monomer for synthesis of polyimide, were derived from maleic anhydride and 2,5-dimethylfuran as the bio-derived monomers with the new approach. The obtained mellophanic dianhydride is used to synthesize the fully bio-based poly(amic acid) using 4-aminocinnamic acid dimer as the bio-based aromatic diamine monomer. For controlling the solubility of polyimide, thermal or chemical imidizations are carried out by using stepwise heating method or acetic anhydride/pyridine treatment, respectively. Thermally imidized polyimides show low solubility for organic solvent, however, chemically-imidized polyimide show good solubility for N-methyl-2-pylloridione, dimethylsulfoxide, and N,N-dimethylformamide. In addition, all the obtained polymers show high heat resistance properties, 10 % decomposed temperature (T d10), of poly(amic acid) is 331 °C, while T d10 of polyimides are 389 °C regardless of imidization processes. Thus, fully bio-based polyimides having high thermostability is developed for the first time.

Biosourced Aromatic Derivatives in the Upcycling of Recycled PET: Mellophanic Dianhydride as a Chain Extender

“…24−28 Recently, a synthesis from bio-based dimethylfuran and maleic anhydride has been proposed (Figure 1b), and the process includes an oxidation step performed with potassium permanganate. 29 To the best of our knowledge, MEDA is actually used only in the preparation of polyimides. 24,29 We now propose the use of MEDA as a bio-based chain extender for R-PET as an alternative to PMDA.…”

“…29 To the best of our knowledge, MEDA is actually used only in the preparation of polyimides. 24,29 We now propose the use of MEDA as a bio-based chain extender for R-PET as an alternative to PMDA. The sustainable synthesis of MEDA starting from tetracarboxylic acid derivatives, obtained from aldaric acids and diethyl fumarate (Figure 1, this work), 18,19 proceeds efficiently without the need for oxidation steps and the use of high valence transition metals as a catalyst, preserving all of the six carbon atoms in the aldaric acid precursor.…”

High Performance Biomass-Based Polyimides for Flexible Electronic Applications

“…13,18−22 Kaneko and co-workers discovered biobased PIs with a high thermal stability using the fully biobased diamines prepared from 4-aminocinnamic acid (4ACA), which was derived from glucose utilizing genetically modified Escherichia coli. 19,23,24 Later, Liou and his co-workers prepared the hybrid films of PI/titanium or PI/zirconia hybrids derived from 4ACA, which exhibited a high transparency and tunable energy level for transparent memristors. 25 On the other hand, Chen and co-workers prepared thermally stable biobased PIs using the diamines and dianhydrides by modification of isomannide, which was one of the isomers of the sugar-derived heterocyclic compound of 1,4:3,6-dianhydrohexitolsis.…”

“…Polyimides (PIs) with outstanding thermal stability, chemical resistance, mechanical endurance, as well as decent and stable dielectric properties were widely investigated. , For example, we developed PIs with double-stranded heterocycle structures for the substrate and dielectric layer in flexible organic field-effect transistors (OFETs), which showed an extremely low coefficient of thermal expansion and a high glass transition temperature. The sustainable development of biobased PIs led to the construction of high performance and flexible electronic devices. ,− Kaneko and co-workers discovered biobased PIs with a high thermal stability using the fully biobased diamines prepared from 4-aminocinnamic acid (4ACA), which was derived from glucose utilizing genetically modified Escherichia coli. ,, Later, Liou and his co-workers prepared the hybrid films of PI/titanium or PI/zirconia hybrids derived from 4ACA, which exhibited a high transparency and tunable energy level for transparent memristors . On the other hand, Chen and co-workers prepared thermally stable biobased PIs using the diamines and dianhydrides by modification of isomannide, which was one of the isomers of the sugar-derived heterocyclic compound of 1,4:3,6-dianhydrohexitolsis .…”

Self-Standing Nanomembranes of Super-Tough Plastics

“…These polymers exhibit high performance owing to the interaction among the aromatic rings, various imide rings, and amide bonds. − Despite having such high performance, most aromatic polymers have the disadvantage of low toughness owing to their high rigidity. Recently, biobased high-performance plastics were developed as superstrong optically transparent plastics of polyimides − and polyamides from an aromatic bioproduced resource, photodimer derivatives of 4-aminocinnamic acid (4ACA), − which is produced from genetically manipulated Escherichia coli to realize a sustainable society. − Specifically, the biobased polyamides had higher thermal and mechanical stability compared to conventional organic glasses, such as poly­(ethylene terephthalate), poly­(methyl methacrylate), polycarbonates, , cycloolefin polymers, and nanocellulose films . However, in a previous study, only fibers could be obtained, and a method for fabricating high-strength films was not established.…”