Synthesis and properties of a novel bio‐based benzoxazine resin with excellent low‐temperature curing ability

Zhan, Zuomin; Yan, Hongqiang; Yin, Ping; Cheng, Jie; Fang, Zhengping

doi:10.1002/pi.5957

Cited by 36 publications

(43 citation statements)

References 39 publications

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“…Andreu et al [52] discussed the effect of acidic groups on the polymerization process of benzoxazine monomers and considered that the polymerization temperature was not related to the electronic effect of side groups, but related to the acidity of substituents, which catalyzed the ring-opening reaction by increasing the concentration of oxonium species. Zhan et al [53] proposed that both O atoms with strong electronegativity in hydroxyl, carboxyl and furan rings and N atoms in amino groups can act as sites for hydrogen bonds in polymer chains. The existence of hydrogen bonds could promote the ring-opening of the oxazine ring too.…”

Section: Effect Of Acidic Functionalitymentioning

confidence: 99%

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Recent Advances in Flame Retardant Bio-Based Benzoxazine Resins

Ding¹,

Wang²,

Song³

et al. 2022

Journal of Renewable Materials

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Benzoxazines have attracted wide attention from academics all over the world because of their unique properties. However, most of the production and preparation of benzoxazine resins depends on petroleum resources now, especially bisphenol A-based benzoxazine. Therefore, owing to the environmental impacts, the development of bio-based benzoxazines is gaining more and more interest to substitute petroleum-based benzoxazines. Similar to petroleum-based benzoxazines, most of bio-based benzoxazines suffer from flammability. Thus, it is necessary to endow bio-based benzoxazines with outstanding flame retardancy. The purpose of this review is to summarize the latest advance in flame retardant bio-based benzoxazines. First, three methods of the synthesis of bio-based benzoxazines are introduced briefly. Furthermore, the curing mechanism of benzoxazine and the effect of branched chains on the curing behavior are also discussed and summarized. Subsequently, this review focuses on fully bio-based benzoxazines, partly bio-based benzoxazines, and bio-based benzoxazine composite materials in terms of flame retardancy as well as thermal stability and some other special properties. Finally, we give a brief comment on the challenges and prospects of the future development of flame retardant bio-based benzoxazines.

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Section: Effect Of Acidic Functionalitymentioning

confidence: 99%

“…Zhan et al [53] synthesized diphenolic acid-based benzoxazines with furfurylamine (DPA-F) or aniline (DPA-A) (Fig. 7) and compared with traditional fossil-based benzoxazine using bisphenol A and aniline (BPA-A).…”

Section: Effect Of Long-branched Chainsmentioning

confidence: 99%

Recent Advances in Flame Retardant Bio-Based Benzoxazine Resins

Ding¹,

Wang²,

Song³

et al. 2022

Journal of Renewable Materials

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“…On the other hand, bio-based benzoxazines can be prepared by bio-based phenols and amines instead of petroleum-based ones. Until now, bio-based polybenzoxazine ( Salum et al, 2018 ; Zhan et al, 2019 ; Lu et al, 2020 ; Zhan et al, 2020 ; Cai et al, 2021 ; Machado et al, 2021 ; Zhang et al, 2022 ) resins have been successfully prepared by natural phenols (cardanol ( Appavoo et al, 2020 ), urushiol ( Chen et al, 2021b ), eugenol ( Zhu et al, 2019 ), resorcinol ( Arnebold et al, 2014 ), guaiacol ( Phalak et al, 2017 ), bisguaiacol F ( Periyasamy et al, 2016 ), phloretic acid ( Kirubakaran et al, 2020 ) ( Zhang et al, 2019a ), and resveratrol ( Zhang et al, 2019b )) and natural amines [( Zhu et al, 2020a ), stearyl amine ( Zhao et al, 2022 ), and rosin-based amines ( Liu et al, 2017 ) and ( Alhwaige et al, 2019) ].…”

Section: Introductionmentioning

confidence: 99%

Metal Ion-Catalyzed Low-Temperature Curing of Urushiol-Based Polybenzoxazine

et al. 2022

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In this work, urushiol-based polybenzoxazine is cured by the Lewis acid (FeCl3, AlCl3, and CuCl2) at low temperature instead of high thermal curing temperature. The effect of the Lewis acid on structures and properties of the polymers is revealed. The relating urushiol-based benzoxazine monomer (BZ) was synthesized by natural urushiol, formaldehyde, and n-octylamine. The monomer was reacted with the Lewis acid with a molar ratio of 6:1 (Nmonomer: NMetal) at 80°C to obtain films that can be cured at room temperature. The chemical structures of benzoxazine monomers were identified by Fourier-transform infrared spectroscopy (FTIR) and 1H nuclear magnetic resonance spectroscopy (1H-NMR). The interaction between the metal ion and the polymers is revealed by X-ray photoelectron spectroscopy (XPS) and attenuated total reflectance-FTIR (ATR-FTIR). The effect of the Lewis acid on the mechanical properties, wettability, and thermal stability was investigated. The results show that the benzoxazine cured by Cu2+ has a better performance than that cured by Al3+ and Fe3+.

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“…1–4 Polybenzoxazines are derived from heterocyclic bis-1,3-benzoxazine monomers that undergo cationic ring opening polymerisation at higher temperatures in the absence of catalyst without releasing any by-products, leading to form 3D cross-linked network structure. 5–7 The formation of hydrogen bonding interaction results between the phenol and tertiary amine within the network structure contributes to number of useful properties required for different high-performance applications, namely, high glass transition temperature (T g ), high thermal stability, low surface energy, low water absorption, excellent dimensional stability, high flame retardance and good dielectric behaviour. 7–12…”

Section: Introductionmentioning

confidence: 99%

“…5–7 The formation of hydrogen bonding interaction results between the phenol and tertiary amine within the network structure contributes to number of useful properties required for different high-performance applications, namely, high glass transition temperature (T g ), high thermal stability, low surface energy, low water absorption, excellent dimensional stability, high flame retardance and good dielectric behaviour. 7–12…”

Section: Introductionmentioning

confidence: 99%

Thermal behaviour of benzoxazine blends based on epoxy and cyanate ester

Krishnasamy

Arumugam

Iqbal

et al. 2021

Polymers and Polymer Composites

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In the present work, an attempt has been made to develop high-performance polymeric hybrid binary blends of epoxy/benzoxazine and benzoxazine/cyanate ester with varying weight percentages (25/75, 50/50 and 75/25 wt%) of resins, namely, bisphenol-F epoxy resin (DGEBF), benzoxazines [bisphenol–F/aniline (BF-a) and imidazole core-based bisphenol/aniline (IBP-a)] and cyanate ester [bisphenol-F bifunctional cyanate ester (BF-CE)]. The molecular structure, polymerisation temperature/cure behaviour, glass transition temperature (Tg) and thermal stability of the neat polymeric matrices and binary hybrid blends of polymeric matrices were characterised using different analytical techniques, viz. Fourier Transform infra-red spectroscopy (FTIR), Nuclear Magnetic Resonance spectroscopy (NMR), Differential Scanning Calorimetry (DSC) and thermogravimetric analysis (TGA). Among the binary hybrid blends, the lowest polymerisation temperatures (Tp) were noticed in the case of blends of epoxy/benzoxazine were 219°C for DGEBF/BF-a (25/75 wt%) and 170°C for DGEBF/IBP-a (25/75 wt%). Similarly, in the case of blends of benzoxazine/cyanate ester, the lowest values of Tp observed were 155°C and 153°C for BF-a/BF-CE (75/25 wt%) and IBP-a/BF-CE (75/25 wt%), respectively. The highest values of Tg observed for the blends of epoxy/benzoxazine were 175°C and 254°C for DGEBF/BF-a (25/75 wt%) and DGEBF/IBP-a (25/75 wt%), respectively. Whereas, the highest values of Tg observed in the case of blends of benzoxazine/cyanate ester were 234°C and 278°C for BF-a/BF-CE (25/75 wt%) and IBP-a/BF-CE (75/25 wt%), respectively. From the TGA results of blends, the maximum degradation temperature (Tmax) and limiting oxygen index (LOI) value calculated from the char yield, which ascertain that almost all the binary hybrid blends of epoxy/benzoxazine and benzoxazine/cyanate ester possess good flame retardant behaviour.

show abstract

Synthesis and properties of a novel bio‐based benzoxazine resin with excellent low‐temperature curing ability

Cited by 36 publications

References 39 publications

Recent Advances in Flame Retardant Bio-Based Benzoxazine Resins

Recent Advances in Flame Retardant Bio-Based Benzoxazine Resins

Metal Ion-Catalyzed Low-Temperature Curing of Urushiol-Based Polybenzoxazine

Thermal behaviour of benzoxazine blends based on epoxy and cyanate ester

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