High-temperature resistant water-soluble polymers derived from exotic amino acids

Dwivedi, Sumant; Nag, Aniruddha; Sakamoto, S.; Funahashi, Yasuyoshi; Harimoto, Toyohiro; Takada, Kenji; Kaneko, Tatsuo

doi:10.1039/d0ra06620f

Cited by 12 publications

(13 citation statements)

References 22 publications

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“…Figure b shows the optimized dimer structures. The bending angle of αATA-Me at 156° indicated an almost straight building block structure . On the other hand, βATA-Me and δATA-Me exhibited bending angles of 70 and 101°, respectively, indicating the introduction of bending structures to the polymer backbone.…”

Section: Resultsmentioning

confidence: 99%

“…Recently developed biobased polyimides synthesized from microorganism-metabolized 4-aminocinnamic acid (4ACA) dimer and various tetracarboxylic acid dianhydrides showed high heat resistance and transparency . Soluble biobased polyimides have also been synthesized from bending tetracarboxylic acid dianhydrides or by modifying the carboxylic acid side chains. , The dimers of cinnamic acid generate various structural isomers, some of which may be bending structure candidates that induce high solubility.…”

Section: Introductionmentioning

confidence: 99%

“…14 Soluble biobased polyimides have also been synthesized from bending tetracarboxylic acid dianhydrides or by modifying the carboxylic acid side chains. 15,16 The dimers of cinnamic acid generate various structural isomers, some of which may be bending structure candidates that induce high solubility.…”

Section: ■ Introductionmentioning

confidence: 99%

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Soluble Biobased Polyimides from Diaminotruxinic Acid with Unique Bending Angles

et al. 2021

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Biobased diamines with unique bending angles, βand δ-type truxinic acids, were prepared from functionalized 4nitrocinnamic acid derivatives via solid-state photodimerization and further chemical modification. The obtained diamines were polymerized with tetracarboxylic acid dianhydrides to produce soluble polyimides via chemical imidization at a high efficiency. The obtained δ-type-based polyimides exhibited a high thermostability at 10% weight loss temperature of ∼415 °C and good solubility in organic solvents. Most of the polyimides were soluble in chloroform and dichloromethane, as well as polar organic solvents. Tensile test results showed that biopolyimide films from cyclobutanetetracarboxylic dianhydride exhibited ∼10.2% elongation at break, indicating high flexibility.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Soluble Biobased Polyimides from Diaminotruxinic Acid with Unique Bending Angles

et al. 2021

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“…[5] In case that the side groups are ionic in the salt with alkaline metals, the BPIs became water-soluble with ultrahigh solubilities over 66 wt%. [6] The photodimers as monomers are truxillic acid derivatives, where the central cyclobutane ring is sandwiched between the nearest-neighboring anilines to provide a rigid triple-ring backbone to the resulting BPI (Figure 1). The nonplanar cyclobutane ring has a V-shape with a fixed angle of 156°, and it is unable to form a rod backbone but can form a bending architecture.…”

Section: Introductionmentioning

confidence: 99%

“…Biopolyimide (BPI) films derived from photodimers of microbial 4‐aminocinnamic acid exhibit high optical transparency, thermostability, and mechanical toughness [5] . In case that the side groups are ionic in the salt with alkaline metals, the BPIs became water‐soluble with ultrahigh solubilities over 66 wt% [6] . The photodimers as monomers are truxillic acid derivatives, where the central cyclobutane ring is sandwiched between the nearest‐neighboring anilines to provide a rigid triple‐ring backbone to the resulting BPI (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Orientation Analysis of Polymer Chains in Optically Transparent Biopolyimides Having Rigid and Bending Backbones

et al. 2021

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Optically transparent and heat-resistant polymer films are useful in the field of organic glasses usable for electric insulators for panels, windows, optical devices, etc. A series of biopolyimides having non-π-conjugated backbones prepared using a renewable diamine, 4,4'-diaminotruxillic acid dimethyl esters, and various dianhydride monomers were prepared and cast onto substrates to form transparent films with high heat resistances and good electric resistance. The second order orientation coefficients (P 200 ) of the biopolyimide films were evaluated by polarized attenuated total reflection Fouriertransform infrared spectroscopy, and the P 200 values for the CÀ N stretching vibrations at a wavenumber of 1365 cm À 1 displayed a good correlation with that for the aromatic CÀ C stretching at 1510 cm À 1 , regardless of the dianhydride structure. The in-plane/out-of-plane birefringence and coefficients of linear thermal expansion exhibited strong correlations with P 200 except for those of a few samples. Most of the biopolyimide films exhibited good transparencies with low birefringence and high electric resistance, which are applicable to flexible substrates with a low coefficient of thermal expansion for panel displays.

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Water Soluble Polymers

Vandenbrande

Brown

Arrington

et al. 2023

Encyclopedia of Polymer Science and Technology

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Water‐soluble polymers (WSPs) represent a diverse class of macromolecules, and this diversity arises from the breadth of functionality derived from both natural and synthetic sources. Nature provides abundant WSPs through biosynthetic pathways in plants, animals, and fungi, and biological processes yield precisely controlled and well‐defined structures. Polymer chemists strive to develop synthetic methods that mimic the precision of natural processes. Monomers that are derived from petroleum feedstocks together with naturally sourced monomers provide a rich catalog of WSP precursors. Monomer structure, reactivity, concentration, sequence control, and reaction conditions influence polymeric microstructures, solubility, and aqueous solution structure. This article provides an overview of WSP fundamentals and highlights recent advancements in natural, nonionic, ionic, associative, and high‐performance WSPs. Recent advances in the design and performance of WSPs have critically improved the technological impact of filtration processes, water purification, drilling efficiency, and pharmaceutical applications. From modulating the rheological and filtration properties to establishing novel drug delivery systems through controllable self‐assembly, WSPs represent a critical enabling field for many emerging and diverse applications. WSPs will help to address many of the emerging challenges of our times, from energy generation and storage to water availability and next‐generation life‐saving medical technologies. This article will point to the potential impacts based on fundamental structure‐property‐processing relationships.

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High-temperature resistant water-soluble polymers derived from exotic amino acids

Abstract: High-performance water-soluble polymers have a wide range of applications from engineering materials to biomedical plastics. This article discusses the synthesis of water-soluble polyimide from bio-based monomers.

Cited by 12 publications

References 22 publications

Soluble Biobased Polyimides from Diaminotruxinic Acid with Unique Bending Angles

Soluble Biobased Polyimides from Diaminotruxinic Acid with Unique Bending Angles

Orientation Analysis of Polymer Chains in Optically Transparent Biopolyimides Having Rigid and Bending Backbones

Water Soluble Polymers

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