Smart Synthesis of High-Performance Thermosets Based on ortho-Amideâ€“Imide Functional Benzoxazines

Zhang, Kan; Ishida, Hatsuo

doi:10.3389/fmats.2015.00005

Cited by 28 publications

(32 citation statements)

References 25 publications

(26 reference statements)

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“…In this study, the hydrogen bonding behavior of two isomeric amide‐containing benzoxazines, substituted at the para and ortho position, are studied by FT‐IR. These results complement not only the long hypothesized existence of an intramolecular five‐membered‐ring hydrogen bond in o HBA‐a proposed in previous papers but also those more recently reported using NMR techniques . It must be highlighted that to make this spectroscopic study fully reliable much emphasis has been paid on obtaining highly purified benzoxazine resins.…”

Section: Introductionsupporting

confidence: 87%

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Study of the Effects of Intramolecular and Intermolecular Hydrogen‐Bonding Systems on the Polymerization of Amide‐Containing Benzoxazines

Han

Zhang

Ishida

et al. 2017

Macro Chemistry & Physics

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Pure para and ortho position amide benzoxazines, pHBA-a and oHBA-a, are synthesized. The hydrogen bonding interactions occurring in pHBA-a and oHBA-a are studied by Fourier transform infrared (FT-IR) spectroscopy and proton nuclear magnetic resonance ( 1 H NMR) spectroscopy. FT-IR results show that, while pHBA-a presents intermolecular hydrogen bonding interactions, oHBA-a exhibits an intramolecular five-membered-ring hydrogenbonding system between the NH in the amide group and the oxygen in the oxazine ring. Differential scanning calorimetry (DSC) is used to study the thermal properties of the resins and their respective polymers. A deeper understanding of the hydrogen bond interactions in this family of resins is attempted to have better insights on how these systems influence the polymerization behavior not only with respect to the polymerization temperature but also with respect to the propagation step.

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Section: Introductionsupporting

confidence: 87%

“…Later, Zhang and co‐workers found that the ortho ‐amide‐imide functional benzoxazine and ortho ‐norbornene functional benzoxazine monomers showed milder synthesis condition (shorter reaction time with high yield) as compared to para counterpart. Furthermore, the corresponding ortho ‐functionalized polymer showed higher T g …”

Section: Introductionmentioning

confidence: 99%

Study of the Effects of Intramolecular and Intermolecular Hydrogen‐Bonding Systems on the Polymerization of Amide‐Containing Benzoxazines

Han

Zhang

Ishida

et al. 2017

Macro Chemistry & Physics

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“…Robust mechanical performance, especially high T g values, low flammability, high hydophobicity, rich hydrogen bondings etc . were obtained using phenolphthalein, aromatic ketone, imide, amide, and nitrile group containing phenols or amines . Likewise, benzoxazines from renewable reagents were synthesized, successfully .…”

Section: The Journey Of Phenolicsmentioning

confidence: 99%

The Journey of Phenolics from the First Spark to Advanced Materials

Kışkan

Yaǧcı

2019

Israel Journal of Chemistry

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The emergence, historical and recent developments of phenolic resins are reviewed. The history of the invention of the first man made plastics and a short bibliography of the inventor Leo H. Baekeland is provided. Moreover, the basic chemistry of phenol‐formaldehyde resins, as synthesis of resol and novolak, their structures, variations, and curing are discussed. Modification of these resins and molecular designs for specific applications in retro perspective are highlighted. This review also provides a comprehensive account on the development of benzoxazine resins as an alternative to classical phenolics. In addition to the benzoxazine synthesis and their curing mechanism, special monomers and polybenzoxazine precursors as curable thermoplastics are reviewed. Besides classical chemicals, the potential of renewables for phenolic resin production is also highlighted. Finally, the relative advantages and disadvantages of these systems are discussed and their future potentials are presented.

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“…In fact, it is now well known that the introduction of electron-withdrawing or electron-donating groups on the structural skeleton of benzoxazine monomers can greatly affect their reactivity by activating the ring-opening or stabilizing the intermediates [27]. Indeed, the catalyst effect of neighboring groups accelerating benzoxazine polymerization has been clearly shown in the case of carboxylic acid- [28], hydroxyl- [29], and amide [30] containing benzoxazine monomers. Moreover, the substitution on the ortho-position was found to further stimulate and activate the ring-opening polymerization when compared to its para-substituted counterpart as well in the case of a methylol functional benzoxazine [23,31] as in the case of an ortho-amide-imide functional benzoxazine [30].…”

Section: Introductionmentioning

confidence: 99%

Cerium Salts: An Efficient Curing Catalyst for Benzoxazine Based Coatings

et al. 2020

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The effect of three different cerium salts (Ce(NO 3 ) 3 ·6H 2 O, CeCl 3 ·7H 2 O and Ce(OOCCH 3 ) 3 ·5H 2 O) on the ring-opening polymerization (ROP) of a model diamine-based benzoxazine (4EP-pPDA) was investigated. With the incorporation of the cerium salts, the curing temperature of 4EP-pPDA is reduced substantially, and the glass transition temperatures of the resulting networks are increased significantly. The three cerium salts exhibit different catalytic activities, which were analyzed by FT-IR, NMR, and energy-dispersive X-ray (EDX). Ce(NO 3 ) 3 ·6H 2 O was found to exhibit the best catalytic effect, which seems to be related to its better dispersibility within 4EP-pPDA benzoxazine precursors.

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Smart Synthesis of High-Performance Thermosets Based on ortho-Amideâ€“Imide Functional Benzoxazines

Cited by 28 publications

References 25 publications

Study of the Effects of Intramolecular and Intermolecular Hydrogen‐Bonding Systems on the Polymerization of Amide‐Containing Benzoxazines

Study of the Effects of Intramolecular and Intermolecular Hydrogen‐Bonding Systems on the Polymerization of Amide‐Containing Benzoxazines

The Journey of Phenolics from the First Spark to Advanced Materials

Cerium Salts: An Efficient Curing Catalyst for Benzoxazine Based Coatings

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