High-performance poly(benzoxazole/benzimidazole) bio-based plastics with ultra-low dielectric constant from 3-amino-4-hydroxybenzoic acid

Nag, Aniruddha; Ali, Mohamed E.A.; Watanabe, Makoto; Singh, Maninder; Amornwachirabodee, Kittima; Kato, Shunsuke; Mitsumata, Tetsu; Takada, Kenji; Kaneko, Tatsuo

doi:10.1016/j.polymdegradstab.2019.01.036

Cited by 26 publications

(17 citation statements)

References 29 publications

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“…Previously reported poly(PBO‐ co ‐PBI)s, synthesized via the copolymerization of AHBA with DABA, where polybenzoxazole (PBO) incorporation had a strong R‐effect on the PBI chains to reduce the H‐bond energy between interchain imidazoles, resulted in a monotonous decrease in T d10 from 716 to 622 °C, with an increasing PBO composition. [ 54 ] This supports our results, in which the H‐bonding energy was found to increase after the incorporation of ABA to PBIs.…”

Section: Resultssupporting

confidence: 90%

Ultrahigh Thermoresistant Lightweight Bioplastics Developed from Fermentation Products of Cellulosic Feedstock

Nag

Ali

Kawaguchi

et al. 2020

Advanced Sustainable Systems

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Production of bioplastics from renewable biological resources is a prerequisite for the development of a circular and sustainable society. Current bioplastics are mostly heat‐sensitive aliphatic polymers, requiring thermoresistant aromatic bioplastics. Herein, 3‐amino‐4‐hydroxybenzoic acid (AHBA) and 4‐aminobenzoic acid (ABA) are produced from kraft pulp, an inedible cellulosic feedstock, using metabolically engineered bacteria. AHBA is chemically converted to 3,4‐diaminobenzoic acid (DABA); subsequently, poly(2,5‐benzimidazole) is obtained by the polycondensation of DABA and processed into an ultrahigh thermoresistant film. The copolymerization of DABA with a small amount of ABA dramatically increases the degradation temperatures of the resulting films (over 740 °C) to yield the most thermoresistant plastic on record. Density functional theory calculations indicate that the incorporation of ABA strengthens the interchain hydrogen bonds between aromatic imidazole rings. Thus, an alternative organic molecular design is proposed for thermoresistant plastics without using heavy inorganics, although continuous aromatic heterocycles are widely considered ideal for polymer thermoresistance. This innovative macromolecular design increases thermoresistance and can be widely applied to well‐processable plastics for the production of lightweight materials and is expected to contribute to the development of a more sustainable society.

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Section: Resultssupporting

confidence: 90%

Ultrahigh Thermoresistant Lightweight Bioplastics Developed from Fermentation Products of Cellulosic Feedstock

Nag

Ali

Kawaguchi

et al. 2020

Advanced Sustainable Systems

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“…If the macromolecular backbone is too rigid, processing becomes difficult in some cases. Considering the good processability of PBI, as shown in previous reports, 9,13 it was hypothesized that the continuous structure of benzimidazole units might be effective for film preparation.…”

Section: Results and Dicussionsmentioning

confidence: 85%

Stepwise copolymerization of polybenzimidazole for a low dielectric constant and ultrahigh heat resistance

et al. 2022

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“…For A4B2-benzoxazole, the formation of the benzoxazole linkage is further confirmed by the resonances at 175.3 and 147.9 ppm, which originate from the carbon atoms of the benzoxazole linkage. 30,31,34 Carbon atoms on the benzene ring are located from 136.9 to 96.1 ppm. The signals at 68.5 and 33.3 ppm are assigned to methylene carbon and quaternary carbon, respectively.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Synthesis of a Stable Benzoxazole Gel from an Imine Gel for Adsorption and Catalysis

Chen

Yang

et al. 2021

Langmuir

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Developing stable gel materials for adsorption and catalysis is one of the major themes of gel materials. However, it has been proven to be challenging to achieve them from small molecules. Herein, an imine gel is developed from tetra-aldehyde 4-{2,2-bis[(4-formylphenoxy)methyl]-3-(4-formylphenoxy)propoxy}benzaldehyde (A4) and 3,3′-dihydroxybenzidine (B2) based on dynamic covalent chemistry. The unstable A4B2-imine gel is further converted into a stable aromatic benzoxazole-linked A4B2-benzoxazole gel via oxidative cyclization, which has significantly improved chemical stability under acidic and basic conditions. Benefiting from the stability under acidic conditions, the A4B2-benzoxazole gel is used for Pd(II) adsorption and the adsorption capacity is 250 mg g–1. After PdCl2 immersion and reduction, palladium nanoparticles with a size distribution of 1.3–14.7 nm are encapsulated by the network structure of the stable porous benzoxazole gel matrix. The Pd@A4B2-benzoxazole gel exhibits high catalytic activity toward the reduction of toxic hexavalent chromium Cr(VI) (reaction rate constant = 0.0377 min–1), while there is no significant decrease in the catalytic efficiency after five cycles.

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High-performance poly(benzoxazole/benzimidazole) bio-based plastics with ultra-low dielectric constant from 3-amino-4-hydroxybenzoic acid

Cited by 26 publications

References 29 publications

Ultrahigh Thermoresistant Lightweight Bioplastics Developed from Fermentation Products of Cellulosic Feedstock

Ultrahigh Thermoresistant Lightweight Bioplastics Developed from Fermentation Products of Cellulosic Feedstock

Stepwise copolymerization of polybenzimidazole for a low dielectric constant and ultrahigh heat resistance

Synthesis of a Stable Benzoxazole Gel from an Imine Gel for Adsorption and Catalysis

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