Two photosensitive chalcone-based benzoxazine monomers and their high-performance polymers from renewable sources

Feng, Zijian; Zeng, Ming; Tan, Dengru; Lu, Xiang; Shen, Yu-Fang; Xu, Qingyu; Meng, Dawei

doi:10.1007/s10853-022-06923-4

Cited by 12 publications

(11 citation statements)

References 60 publications

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“…Among the literature that reported benzoxazine resins based on green strategies, 9–27,29–31,47–72 only three of them reported static mechanical properties of the resins (Table S1), however, these resins do not show high thermal resistance ( T g ≤ 193 °C, T di ≤ 381 °C). Figure 10B shows the stress–strain curve of poly(CT‐fa) , from which poly(CT‐fa) is known to have excellent tensile strength (51.60 ± 0.27 MPa), tensile modulus (3.32 ± 0.03 GPa) and elongation at break (1.95 ± 0.02%).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of new biobased benzoxazine through green strategy and its polybenzoxazine resin with high thermal resistance and mechanical strength

Liu

Yuan

Liang

et al. 2023

Journal of Polymer Science

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Benzoxazine resins from benzoxazine monomers synthesized with green strategies often do not have high thermal resistance and mechanical strength. Herein, starting from renewable resources citraconic anhydride, furfurylamine and tyramine, a new benzoxazine monomer (CT‐fa) was synthesized and purified in green solvents (ethanol and ethyl acetate), which has excellent molding processability reflected by low melting point (84.9 °C) and low curing temperature (207–245 °C). More attractively, the cured CT‐fa resin (poly(CT‐fa)) has both high glass transition temperature (281 °C) and high initial thermal decomposition temperature (407 °C), the former is higher than those of all monofunctional benzoxazine resins synthesized though green strategies in literature, and the latter is even higher than those of all benzoxazine resins synthesized by green strategies (SCI database). In addition, poly(CT‐fa) also has high storage modulus (3955 MPa) and good tensile strength (51.60 MPa). These attractive properties demonstrate that poly(CT‐fa) is a promising green high performance resins.

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Section: Resultsmentioning

confidence: 99%

Synthesis of new biobased benzoxazine through green strategy and its polybenzoxazine resin with high thermal resistance and mechanical strength

Liu

Yuan

Liang

et al. 2023

Journal of Polymer Science

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“…The chemical shifts at 1.27–1.38 and 2.18–2.32 ppm correspond to the –CH 3 and –CH 2 – bonds of the spirobisindane structure. For TSBZBC, the chemical shifts of the cross-linkable benzoxazine group were confirmed by specific –CH 2 – signals of the oxazine ring, namely Ar-CH 2 -N and O-CH 2 -N, which appeared at 4.68 and 5.31 ppm [ 47 ], respectively, at positions f and e, respectively ( Figure S1 ). For TSBZBN, the oxazine ring appeared at 4.73 and 5.33 ppm at positions f and e, respectively ( Figure S2 ).…”

Section: Resultsmentioning

confidence: 99%

Spiro-Twisted Benzoxazine Derivatives Bearing Nitrile Group for All-Solid-State Polymer Electrolytes in Lithium Batteries

Lee

Yeh

et al. 2022

Polymers

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In this study, two nitrile-functionalized spiro-twisted benzoxazine monomers, namely 2,2′-((6,6,6′,6′-tetramethyl-6,6′,7,7′-tetrahydro-2H,2′H-8,8′-spirobi[indeno[5,6-e][1,3]oxazin]-3,3′(4H,4′H)-diyl)bis(4,1-phenylene))diacetonitrile (TSBZBC) and 4,4′-(6,6,6′,6′-tetramethyl-6,6′,7,7′-tetrahydro-2H,2′H-8,8′-spirobi[indeno[5,6-e][1,3]oxazin]-3,3′(4H,4′H)-diyl)dibenzonitrile (TSBZBN) were successfully developed as cross-linkable precursors. In addition, the incorporation of the nitrile group by covalent bonding onto the crosslinked spiro-twisted molecular chains improve the miscibility of SPE membranes with lithium salts while maintaining good mechanical properties. Owing to the presence of a high fractional free volume of spiro-twisted matrix, the –CN groups would have more space for rotation and vibration to assist lithium migration, especially for the benzyl cyanide-containing SPE. When combined with poly (ethylene oxide) (PEO) electrolytes, a new type of CN-containing semi-interpenetrating polymer networks for solid polymer electrolytes (SPEs) were prepared. The PEO-TSBZBC and PEO-TSBZBN composite SPEs (with 20 wt% crosslinked structure in the polymer) are denoted as the BC20 and BN20, respectively. The BC20 sample exhibited an ionic conductivity (σ) of 3.23 × 10−4 S cm−1 at 80 °C and a Li+ ion transference number of 0.187. The LiFePO4 (LFP)|BC20|Li sample exhibited a satisfactory charge–discharge capacity of 163.6 mAh g−1 at 0.1 C (with approximately 100% coulombic efficiency). Furthermore, the Li|BC20|Li cell was more stable during the Li plating/stripping process than the Li|BN20|Li and Li|PEO|Li samples. The Li|BC20|Li symmetric cell could be cycled continuously for more than 2700 h without short-circuiting. In addition, the specific capacity of the LFP|BC20|Li cell retained 87% of the original value after 50 cycles.

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“…Then the IPN films are obtained by the programmed temperature rising method with simultaneous polymerization of crosslinkable group of PPO oligomer and oxazine ring of benzoxazine as well as the electrophilic substitution reaction of furan ring of benzoxazine. Recently, FU based benzoxazine monomers have been designed and synthesized because of its naturally occurring and reactive nature 24–37 . In comparison with the corresponding aniline‐based difunctional benzoxazine resins, the incorporation of less aromatic furan ring not only increases the reactivity of benzoxazines, but also reduces the molecular polarity of the resulting polybenzoxazines, leading to the enhancement of processing and dielectric properties 33–37 .…”

Section: Introductionmentioning

confidence: 99%

“…Recently, FU based benzoxazine monomers have been designed and synthesized because of its naturally occurring and reactive nature. [24][25][26][27][28][29][30][31][32][33][34][35][36][37] In comparison with the corresponding aniline-based difunctional benzoxazine resins, the incorporation of less aromatic furan ring not only increases the reactivity of benzoxazines, but also reduces the molecular polarity of the resulting polybenzoxazines, leading to the enhancement of processing and dielectric properties. [33][34][35][36][37] Besides, the reactive furan group can increase the cross-linking density of the resulting polymers, and further enhance their T g s and thermal stability due to the formation of furfurylamine Mannich bridge.…”

Section: Introductionmentioning

confidence: 99%

“…[24][25][26][27][28][29][30][31][32][33][34][35][36][37] In comparison with the corresponding aniline-based difunctional benzoxazine resins, the incorporation of less aromatic furan ring not only increases the reactivity of benzoxazines, but also reduces the molecular polarity of the resulting polybenzoxazines, leading to the enhancement of processing and dielectric properties. [33][34][35][36][37] Besides, the reactive furan group can increase the cross-linking density of the resulting polymers, and further enhance their T g s and thermal stability due to the formation of furfurylamine Mannich bridge. 31,32 Nevertheless, the relatively high cure temperature (240 C or higher) is still necessary for the polymerization reaction of FU-based benzoxazines.…”

Section: Introductionmentioning

confidence: 99%

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A facile method to fabricate thermally stable methacrylate‐terminated oligo(2,6‐dimethyl‐1,4‐phenylene oxide)/benzoxazine thermosetting resins with low dielectric constants and losses at 10 GHz

Zeng

Tan

Feng

et al. 2023

J of Applied Polymer Sci

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Poly(2,6‐dimethyl‐1,4‐phenylene oxide) (PPO) as a kind of low dielectric polymer has been applied in telecommunications. However, developing PPO based thermosetting resins with good comprehensive properties is highly challenging. Herein, an interpenetrating polymer network (IPN) design strategy for the preparation of methacrylate‐terminated oligo(2,6‐dimethyl‐1,4‐phenylene oxide) (SA9000) based thermosetting resins is presented. Two series of prepolymers are prepared by blending bisphenol A/furfurylamine benzoxazine (B‐f) or bisphenol A/aniline benzoxazine (B‐a) with SA9000. Then the IPN films are fabricated by the programmed temperature rising method with simultaneous polymerization reactions of both SA9000 and benzoxazines. Owing to the intermolecular interactions between SA9000 and benzoxazines, the polymerization peak temperatures of all prepolymers are lower than those of SA9000 and benzoxazines. In comparison with B‐a based films, B‐f/SA9000 films display better miscibility and higher thermal resistances over the entire composition range, due to the strengthened hydrogen bonding and higher cross‐linking density resulting from the presence of furan ring of B‐f. Specifically, B‐f/SA9000 films possess the advantages of low dielectric constants (2.296–2.475) and low‐loss grade dielectric losses (0.00550–0.00683) at 10 GHz. The current work provides a simple and effective path for the fabrication of high‐performance thermosetting PPO resins based on benzoxazine chemistry and IPN structure design.

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Two photosensitive chalcone-based benzoxazine monomers and their high-performance polymers from renewable sources

Cited by 12 publications

References 60 publications

Synthesis of new biobased benzoxazine through green strategy and its polybenzoxazine resin with high thermal resistance and mechanical strength

Synthesis of new biobased benzoxazine through green strategy and its polybenzoxazine resin with high thermal resistance and mechanical strength

Spiro-Twisted Benzoxazine Derivatives Bearing Nitrile Group for All-Solid-State Polymer Electrolytes in Lithium Batteries

A facile method to fabricate thermally stable methacrylate‐terminated oligo(2,6‐dimethyl‐1,4‐phenylene oxide)/benzoxazine thermosetting resins with low dielectric constants and losses at 10 GHz

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