Effect of pyrogallol on the ring-opening polymerization and curing kinetics of a fully bio-based benzoxazine

Li, Xiu; Yao, Hongjie; Lu, Xin; Chen, Chen; Cao, Yuzhu; Xin, Zhong

doi:10.1016/j.tca.2020.178787

Cited by 24 publications

(27 citation statements)

References 33 publications

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“…Zhang et al [41] used naringenin and furfurylamine as reactants to synthesize a fully bio-based benzoxazine and proposed a suitable mechanism of the inherent latent catalyst activity and ring-opening polymerization. Li et al [50] investigated the effect of pyrogallol which served as a phenolic nucleophile on the curing process and kinetics of bio-based benzoxazines with phenol as a contrast. The curing kinetic parameters of E-s and E-s/py were calculated by the Kissinger equation and the Ozawa equation, which showed that the addition of phenolic hydroxyl decreased the apparent activation energy of the curing system.…”

Section: Effect Of Acidic Functionalitymentioning

confidence: 99%

“…The curing kinetic parameters of E-s and E-s/py were calculated by the Kissinger equation and the Ozawa equation, which showed that the addition of phenolic hydroxyl decreased the apparent activation energy of the curing system. Apparent activation energy is calculated according to these two equations, as shown below [50]:…”

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%

Section: Effect Of Acidic Functionalitymentioning

confidence: 99%

Recent Advances in Flame Retardant Bio-Based Benzoxazine Resins

Ding¹,

Wang²,

Song³

et al. 2022

Journal of Renewable Materials

View full text Add to dashboard Cite

show abstract

“…For example, pyrogallol with three equivalent phenolic groups can be produced from carbohydrates, and the phenolic groups in the 2-site could still exist due to the limited Mannich reaction sites, of which the acidity promotes the polymerization of benzoxazine resin. [132][133][134] The benzoxazine resin origin from phloroglucinol with similar structure exhibited superior residual carbon (R 800 of 34.7%-53%), low flammable properties (heat release capacity of 37 J/gÁK, abbreviated as HRC) and low curing temperature when p-aminobenzoic acid was used as the amine source. 135 Furthermore, the carbonyl group in deoxybenzoin is thought to isomerize to produce protons with catalysis effect in lowering the ring-opening polymerization temperature.…”

Section: High Performance Bio-based Benzoxazine Resinmentioning

confidence: 99%

“…In addition to the above monophenols extracted from plants, many other bio‐based bis‐ and multi‐phenol were also explored to prepare benzoxazine, some feedstocks of which have special structure were found to reduce the curing temperature of the resin as well. For example, pyrogallol with three equivalent phenolic groups can be produced from carbohydrates, and the phenolic groups in the 2‐site could still exist due to the limited Mannich reaction sites, of which the acidity promotes the polymerization of benzoxazine resin 132–134 . The benzoxazine resin origin from phloroglucinol with similar structure exhibited superior residual carbon (R 800 of 34.7%–53%), low flammable properties (heat release capacity of 37 J/g·K, abbreviated as HRC) and low curing temperature when p‐aminobenzoic acid was used as the amine source 135 .…”

Section: Bio‐based Benzoxazine Resinmentioning

confidence: 99%

Recent development on bio‐based thermosetting resins

Liu

Zhang

Shun

et al. 2021

Journal of Polymer Science

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Due to the rapid depletion of crude oil and serious environmental pollution, the synthesis of polymers from renewable resource is becoming more and more important. Up to now, a great variety of biomass and bio-based platform compounds have been taken to prepare the polymers. However, as two representative thermosetting resins, epoxy and benzoxazine resin derived from renewable feedstocks only obtain limited attention compared with the popular bio-based plastics, including PLA, PBAT and PHBV etc. The reason might be that the properties of previously reported thermosetting resins directly obtained from biomass are usually unsatisfied, and their application fields are limited. In this paper, the latest development on the synthesis of highperformance bio-based epoxy and polybenzoxazine resins are reviewed. In addition, to further broaden their applications, the functionalization strategies are also summarized. The objective of this work is to help us fully aware the present situation of bio-based thermosetting resins and then promote their faster development, especially practical application.

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“…[ 30 ] Li et al. [ 31 ] used pyrogallol to reduce the exothermic peak temperature of the eugenol/stearylamine based benzoxazine from 254 to 168 °C. In addition, there was good compatibility existed between phenolic nucleophiles and benzoxazine monomers.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Bio‐Based Polybenzoxazine/Pyrogallol/Polyhedral Oligomeric Silsesquioxane Nanocomposites: Low Dielectric Constant and Low Curing Temperature

Zhao

Yuan

Wang

et al. 2021

Macro Materials & Eng

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In this work, a bio-based benzoxazine monomer (C-s) is synthesized from cardanol, stearylamine, and paraformaldehyde through solvent-free method. Pyrogallol is used as a curing catalyst for the ring-opening polymerization of benzoxazine. Differential scanning calorimeter (DSC) results reveal that doping with pyrogallol reduces the exothermic peak temperature (T p ) of C-s from 256 to 174 °C. The polybenzoxazine/pyrogallol/polyhedral oligomeric silsesquioxane (PC-s/py/POSS) nanocomposites are prepared via thermal curing. The doping of aminopropyl isobutyl POSS (POSS-NH 2 ) can reduce the dielectric constant of polybenzoxazine. The dielectric constant of PC-s/py/POSS is 2.64 at 1 MHz when the doping amount of POSS-NH 2 is 10 wt%. The results of thermogravimetric analysis (TGA) and water absorption test indicate that the PC-s/py/POSS nanocomposites possess good thermal stability and water resistance. In summary, the PC-s/py/POSS nanocomposites with low curing temperature and low dielectric constant are expected to be applied to the low dielectric materials for microelectronic applications.

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Effect of pyrogallol on the ring-opening polymerization and curing kinetics of a fully bio-based benzoxazine

Cited by 24 publications

References 33 publications

Recent Advances in Flame Retardant Bio-Based Benzoxazine Resins

Recent Advances in Flame Retardant Bio-Based Benzoxazine Resins

Recent development on bio‐based thermosetting resins

Preparation of Bio‐Based Polybenzoxazine/Pyrogallol/Polyhedral Oligomeric Silsesquioxane Nanocomposites: Low Dielectric Constant and Low Curing Temperature

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