A highly rigid diamine monomer derived from naturally occurring<i>myo</i>-inositol and its use for polyamide synthesis

Sudo, Atsushi; Sugita, Shou

doi:10.1002/pola.28231

Cited by 9 publications

(11 citation statements)

References 41 publications

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“…R4 was chosen based on it being another derivative of the bio-based 4ACA, whereas R1, R2, and R3 were chosen as common aromatic diamines. The rigidity of these bridging diamines aromatic structures was also deemed favorable in terms of molecular weight and thermal resistance for the polymerization of biopolyamides. , …”

Section: Methodsmentioning

confidence: 99%

Anion-Scavenging Biopolyamides from Quaternized 4-Aminocinnamic Acid Photodimers

Phanthuwongpakdee

Babel

Dwivedi

et al. 2020

ACS Sustainable Chem. Eng.

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Anionic pollutants in water, especially radioactive iodide, have gained attention because of their adverse toxic side effects on humans. Recently, an exotic biobased amino acid, 4-amino cinnamic acid (4ACA), has been utilized to produce heat-resistant and UV-degradable biopolyamides. In this research, a multifunctional monomer, 4,4′-di(trimethylamino)-α-truxillic acid (Q4-ATA), was synthesized by the quaternization of 4ACA and was polymerized with various diamines to obtain a series of biopolyamides. All biopolyamides are soluble in aprotic solvents and possess high thermal properties, with 10% weight loss temperatures of 296–329 °C. One application of these cationic biopolyamide-bearing quaternary ammonium was the anion-exchange ability, so they were employed to remove iodide (I–) from the water. PA-R4 was highlighted as an entirely biobased cationic polyamide as its precursors were Q-4ATA and the glucose diamine derivatives. It was calculated to have more than 99% use of renewable sources in the sustainability metric. With 120 min equilibrium time, more than 80% adsorption of 10 mg/L initial I– concentration in 90 °C was confirmed. The ability of our biopolyamides to perform stable anion-exchange processes in various conditions has made them a new, sustainable, and promising system for anionic pollution remediation in water.

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Section: Methodsmentioning

confidence: 99%

Anion-Scavenging Biopolyamides from Quaternized 4-Aminocinnamic Acid Photodimers

Phanthuwongpakdee

Babel

Dwivedi

et al. 2020

ACS Sustainable Chem. Eng.

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“…Until now, a large number of bioactive molecules bearing inositol-derived components were used as building blocks in developing macromolecular backbones containing diols, like polyurethanes [41] or polyamides [42]. It was a matter of time until it would have been used to prepare polyimidic architectures through its incorporation in diamines [15,16,28,40].…”

Section: Pis Derived From Myo-inositol (Mi)mentioning

confidence: 99%

“…For example, myo-inositol was treated with 1,1-dimethoxycyclohexane to yield a heterocyclic compound with three alicyclic units, the central one bearing two free hydroxyl groups [42]. These hydroxyl moieties are further used to introduce two aromatic amine functions through substitution and subsequent reduction reactions [40].…”

Section: Pis Derived From Myo-inositol (Mi)mentioning

confidence: 99%

New High-Performance Materials: Bio-Based, Eco-Friendly Polyimides

Rusu¹,

Abadie²

2021

Polyimide for Electronic and Electrical Engineering Applications

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The development of high-performance bio-based polyimides (PIs) seems a difficult task due to the incompatibility between petrochemical-derived, aromatic monomers and renewable, natural resources. Moreover, their production usually implies less eco-friendly experimental conditions, especially in terms of solvents and thermal conditions. In this chapter, we touch some of the most significant research endeavors that were devoted in the last decade to engineering naturally derived PI building blocks based on nontoxic, bio-renewable feedstocks. In most cases, the structural motifs of natural products are modified toward amine functionalities that are then used in classical or nonconventional methods for PI synthesis. We follow their evolution as viable alternatives to traditional starting compounds and prove they are able to generate eco-friendly PI materials that retain a combination of high-performance characteristics, or even bring some novel, enhanced features to the field. At the same time, serious progress has been made in the field of nonconventional synthetic and processing options for the development of PI-based materials. Greener experimental conditions such as ionic liquids, supercritical fluids, microwaves, and geothermal techniques represent feasible routes and reduce the negative environmental footprint of PIs' development. We also approach some insights regarding the sustainability, degradation, and recycling of PI-based materials.

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“…Our research interest has been focused on the utilization of myo ‐inositol, a naturally occurring cyclic hexaol, as a starting material for polymer synthesis . myo ‐Inositol and its derivatives can be found abundantly in various plants and animal organs.…”

Section: Introductionmentioning

confidence: 99%

“…26,27 Our research interest has been focused on the utilization of myo-inositol, a naturally occurring cyclic hexaol, as a starting material for polymer synthesis. [28][29][30][31][32] myo-Inositol and its derivatives can be found abundantly in various plants and animal organs. Rice bran and bean skins are especially useful sources of myo-inositol because they contain phytic acid, a hexaphosphate of myo-inositol.…”

mentioning

confidence: 99%

Rigid diol bearing 6‐6‐6 fused ring system derived from naturally occurring myo‐inositol and its polyaddition with diisocyanates

Yoshida

Sudo

2017

J. Polym. Sci. Part A: Polym. Chem.

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Naturally occurring myo‐inositol was developed into a highly rigid diol by converting its 3,4‐ and 1,6‐vicinal diols in trans configuration into the corresponding butane‐2,3‐diacetals. The resulting diol bearing 6‐6‐6 fused ring system, in which conformational change is strictly suppressed, was combined with diisocyanates to perform polyadditions. The resulting polyurethanes were analyzed by differential scanning calorimetry, and it was found that their glass transition temperatures were much higher than those of the previously reported myo‐inositol‐derived polyurethanes, which were synthesized from a myo‐inositol‐derived diol bearing 5‐6‐5 fused ring system. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 3798–3803

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A highly rigid diamine monomer derived from naturally occurringmyo-inositol and its use for polyamide synthesis

Cited by 9 publications

References 41 publications

Anion-Scavenging Biopolyamides from Quaternized 4-Aminocinnamic Acid Photodimers

Anion-Scavenging Biopolyamides from Quaternized 4-Aminocinnamic Acid Photodimers

New High-Performance Materials: Bio-Based, Eco-Friendly Polyimides

Rigid diol bearing 6‐6‐6 fused ring system derived from naturally occurring myo‐inositol and its polyaddition with diisocyanates

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