An apigenin-based bio-benzoxazine with three polymerizable functionalities: sustainable synthesis, thermal latent polymerization, and excellent thermal properties of its thermosets

Hao, Boran; Han, Lu; Liu, Yuqi; Zhang, Kan

doi:10.1039/d0py00983k

Cited by 63 publications

(65 citation statements)

References 42 publications

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“…To reduce the carbon foot print, exploration of non-petrochemical feedstocks that are obtained naturally or in bio-wastes is actively sought both as solvent or solvent-free reactions [ 84 ]. These include cardanol (C) [ 85 , 86 , 87 , 88 , 89 , 90 ]; guaiacol (G) [ 89 , 91 , 92 ]; eugenol [ 93 , 94 ]; isoeugenol [ 95 ]; vanillin (V) [ 96 , 97 , 98 ]; umbelliferone (U) [ 99 ]; catechol [ 100 ]; cinnamic, ferulic, coumaric [ 101 , 102 ] and phloretic acid [ 101 , 103 , 104 ]; magnolol [ 105 ]; resveratrol [ 106 ]; humic acid (coal origin) [ 107 ]; daidzein [ 108 ]; naringenin [ 109 ]; arbutin-linked phenol [ 110 ]; levulinic acid based diphenolic acid [ 111 , 112 ]; sesamol [ 113 ]; apigenin [ 84 ] and amines such as stearylamine [ 93 ], dopamine [ 114 ], furfuryl amine (fa) [ 95 , 115 ], aminolysed poly(ethylene terephthalate) [ 116 ] and isomannide diamine (ima) [ 89 ], as shown in Figure 3 .…”

Section: Classification Of Benzoxazine Monomersmentioning

confidence: 99%

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

et al. 2021

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Due to their outstanding and versatile properties, polybenzoxazines have quickly occupied a great niche of applications. Developing the ability to polymerize benzoxazine resin at lower temperatures than the current capability is essential in taking advantage of these exceptional properties and remains to be most challenging subject in the field. The current review is classified into several parts to achieve this goal. In this review, fundamentals on the synthesis and evolution of structure, which led to classification of PBz in different generations, are discussed. Classifications of PBzs are defined depending on building block as well as how structure is evolved and property obtained. Progress on the utility of biobased feedstocks from various bio-/waste-mass is also discussed and compared, wherever possible. The second part of review discusses the probable polymerization mechanism proposed for the ring-opening reactions. This is complementary to the third section, where the effect of catalysts/initiators has on triggering polymerization at low temperature is discussed extensively. The role of additional functionalities in influencing the temperature of polymerization is also discussed. There has been a shift in paradigm beyond the lowering of ring-opening polymerization (ROP) temperature and other areas of interest, such as adaptation of molecular functionality with simultaneous improvement of properties.

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Section: Classification Of Benzoxazine Monomersmentioning

confidence: 99%

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

et al. 2021

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“…[ 9–18 ] In particular, siloxane‐based polybenzoxazines have gained prominence due to their excellent thermal resistance and significant compatibility with organic compounds. [ 13,19–23 ]…”

Section: Introductionmentioning

confidence: 99%

Tuning morphology of siloxane bond‐based polybenzoxazines by controlling the sol–gel and curing processes

Casarino

Bortolato

Estenoz

et al. 2021

Polymer Engineering & Sci

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Novel polybenzoxazine/polysilsesquioxane nanocomposites were synthesized with uniform and reproducible structural morphology, high Tg, and good thermal stability. Polysilsesquioxane was oriented in a nanometer‐size lamellar structure. Benzoxazine monomer based on silane (BA‐3aptms) was synthesized by reaction between bisphenol A, 3‐(trimethoxysilyl)propylamine, and paraformaldehyde in a 1:2:4 molar ratio. Four experimental conditions of the two stage sol–gel process for polysilsesquioxane were studied, and their effect on the material characteristics investigated. In the first stage, hydrolysis was favored, while the second stage mostly consisted of condensation. The reaction condition with the longest hydrolysis time allowed the increase of the concentration of silanol units and the selective condensation, favoring the formation of a higher amount of cage‐like cyclic structures. In addition, this experimental procedure was well controlled so that the sol–gel and oxazine‐ring opening reactions were extremely reproducible from batch to batch. All processes were monitored by Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis and dynamic mechanical thermal analysis, scanning electron and transmission electron microscopies, and X‐ray diffraction. A chemometric approach based on a multivariate curve resolution model was applied to the FTIR spectra, which allowed the identification of four reaction components associated with the sol–gel and the curing processes.

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“…The last year also showed a growing interest in the design of new bio-based BZ monomers and polymers. For instance, Hao et al prepared partially bio-based BZ monomers from apigenin and furfurylamine (Hao et al, 2020). The adopted synthetic route although not fully bio afforded BZ monomers with a unique thermal latent polymerization characteristic due to the presence of intramolecular hydrogen bonds within the molecular structure.…”

Section: Benzoxazine Resinsmentioning

confidence: 99%

Sustainable and Ecofriendly Chemical Design of High Performance Bio-Based Thermosets for Advanced Applications

et al. 2021

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High performance thermosetting resins are targeted in many exigent applications, such as aerospace and marine fields, for the development of lightweight structural composites. Till now, these industries only rely on petroleum-based materials for their supposedly better performances. However, the latest developments in the field suggest otherwise. In fact, many reports confirmed that sustainable and ecofriendly thermosetting polymers can display similar or even better performances. Additionally, exploring alternative renewable feedstock’s to meet the ever increasing demands of these industries is an essential step towards sustainable development. Aiming to unravel the potential of these materials, the present review summarizes the most relevant chemical routes allowing the preparation of fully or partially bio-based thermosetting resins. Meanwhile, the overall performances of these exceptional materials are also compared with their petroleum-based counterparts.

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An apigenin-based bio-benzoxazine with three polymerizable functionalities: sustainable synthesis, thermal latent polymerization, and excellent thermal properties of its thermosets

Abstract: Benzoxazine resins have been constantly attracting attention from both academia and industry attributing to their molecular design flexibility and high performance of its thermoset polymer properties. However, a reduction in...

Cited by 63 publications

References 42 publications

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

Tuning morphology of siloxane bond‐based polybenzoxazines by controlling the sol–gel and curing processes

Sustainable and Ecofriendly Chemical Design of High Performance Bio-Based Thermosets for Advanced Applications

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