Combining naphthoxazines and benzoxazines for non-symmetric curable oxazines by one-pot synthesis

Güngör, Füsun Şeyma; Batı, Bige; Kışkan, Barış

doi:10.1016/j.eurpolymj.2019.109352

Cited by 25 publications

(9 citation statements)

References 59 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Although byproduct and formaldehyde release during the production of polybenzoxazines from their corresponding benzoxazine monomers is limited unlike classical phenolic resin production processes (Scheme ), some benzoxazine monomers could evaporate during curing due to the high polymerization temperatures (160–260 °C) usually applied. − However, in general, those volatile benzoxazines are low molar mass compounds, and actually most of the commercial monomers are solid. In order to reduce evaporation and increase processability, several strategies involving the use of polymeric benzoxazines as main-, side-, and end-chain precursors were proposed. − Additionally, ring-opening polymerization of benzoxazines can be catalyzed effectively by cationic species, acids, and even amines or some salts to reduce the curing temperatures for both energy efficiency and limiting the amount of monomer evaporation. − Although polybenzoxazine synthesis is relatively greener compared to classical phenolic resin production as a consequence of reactive nature of their monomers, high atom economy, and low byproduct emissions, benzoxazine resins are still facing environmental and ecological challenges similar to other fossil resource-based polymers.…”

Section: Introductionmentioning

confidence: 99%

Advanced Thermosets from Sulfur and Renewable Benzoxazine and Ionones via Inverse Vulcanization

Bayram

Kışkan

Demir

et al. 2020

ACS Sustainable Chem. Eng.

Self Cite

View full text Add to dashboard Cite

An unprecedented synthesis of terpolymers from bioderived monomers and elemental sulfur in one-pot is described. In this approach, biosourced compounds, namely, vanilin and furfurylamine-based benzoxazine and ionones (and carvone), and a waste product of petroleum industry, sulfur, were reacted in one pot to produce an advanced thermoset. The inverse vulcanization of these compounds was monitored, and the properties of the obtained terpolymers were characterized via spectral and thermal characterization methods. Moreover, a potential use of the polymers as a Li−S battery cathode was demonstrated, and over 400 mAh/g capacity more than 100 of cycles were observed. Electrochemical impedance spectroscopy studies were used to gain more insight into the lithium storage mechanism before and after cycling.

show abstract

Section: Introductionmentioning

confidence: 99%

Advanced Thermosets from Sulfur and Renewable Benzoxazine and Ionones via Inverse Vulcanization

Bayram

Kışkan

Demir

et al. 2020

ACS Sustainable Chem. Eng.

Self Cite

View full text Add to dashboard Cite

show abstract

“…General formulation of PHB-a/5-aminoindole curing systems Preparation of PHB-a PHB-a was firstly prepared according to a previous report. 22 Melting point: 97°C (from DSC). 1 The structure of PHB-a is shown in (Fig.…”

Section: Methodsmentioning

confidence: 99%

“…[18][19][20][21] Despite the obvious toughening effects reported, this method is complex and time-consuming in the preparation of the benzoxazine precursors. As to the preparation of polymeric benzoxazine precursors, 18 researchers have successfully designed polyallylamine bearing 1,3-benzoxazine moieties in the side chains, 19 polybenzoxazine containing pendent aliphatic chains, 20 main-chain bisphenol-A benzoxazine, 21 oligo(benzoxazine-side-naphthoxazine) 22 and so on. Though the polymeric chain contributes toward the improvement of mechanical properties of the resulting polymer, it is always accompanied by the sacrifice of the thermal properties of polybenzoxazines.…”

Section: Introductionmentioning

confidence: 99%

Improvement of aldehyde‐functional polybenzoxazine processability and mechanical properties achieved by 5‐aminoindole/benzoxazine copolymerization

Yang

Liu

et al. 2020

Polymer International

View full text Add to dashboard Cite

5-Aminoindole is designed for aldehyde-functional benzoxazine (PHB-a) copolymerization due to the special reaction between the indole and aldehyde groups, and the copolymerization with benzoxazine monomers. The curing and mechanical behavior and thermal properties of the cured resins are investigated using Fourier transform infrared spectroscopy, 1 H NMR spectroscopy, differential scanning calorimetry, scanning electron microscopy, dynamic mechanical analysis, tensile tests and thermogravimetric analysis. The resulting networks show better processability and mechanical properties without obvious degradation in thermal performance. The low curing temperature (70°C) of PHB-a is achieved after incorporation of 5-aminoindole. An elongation rate of 2.54% and a forcing break of around 72.3 MPa are achieved, while neat poly(PHB-a) is brittle and failed in the grips. Furthermore, its glass transition temperature is maintained up to 234°C. These findings open a new way to realize low-temperature curing and to improve the mechanical properties of brittle polybenzoxazine resins under the premise of maintaining good thermal stability.

show abstract

“…Nevertheless, the application of PBZ materials has been restricted industrially because the ROP of BZ resins to afford PBZs generally occurs at temperatures between 220 and 280 °C [ 10 , 11 , 12 , 13 , 14 ]. As a result, lowering the exothermic curing temperatures of BZ precursors has become desirable to encourage the use of these materials in industrial applications and academic settings [ 1 , 2 , 3 , 4 , 5 ].…”

Section: Introductionmentioning

confidence: 99%

Microporous Carbon and Carbon/Metal Composite Materials Derived from Bio-Benzoxazine-Linked Precursor for CO2 Capture and Energy Storage Applications

Mohamed

Samy

Mansoure

et al. 2021

IJMS

View full text Add to dashboard Cite

There is currently a pursuit of synthetic approaches for designing porous carbon materials with selective CO2 capture and/or excellent energy storage performance that significantly impacts the environment and the sustainable development of circular economy. In this study we prepared a new bio-based benzoxazine (AP-BZ) in high yield through Mannich condensation of apigenin, a naturally occurring phenol, with 4-bromoaniline and paraformaldehyde. We then prepared a PA-BZ porous organic polymer (POP) through Sonogashira coupling of AP-BZ with 1,3,6,8-tetraethynylpyrene (P-T) in the presence of Pd(PPh3)4. In situ Fourier transform infrared spectroscopy and differential scanning calorimetry revealed details of the thermal polymerization of the oxazine rings in the AP-BZ monomer and in the PA-BZ POP. Next, we prepared a microporous carbon/metal composite (PCMC) in three steps: Sonogashira coupling of AP-BZ with P-T in the presence of a zeolitic imidazolate framework (ZIF-67) as a directing hard template, affording a PA-BZ POP/ZIF-67 composite; etching in acetic acid; and pyrolysis of the resulting PA-BZ POP/metal composite at 500 °C. Powder X-ray diffraction, thermogravimetric analysis, scanning electron microscopy, transmission electron microscopy, and Brunauer–Emmett–Teller (BET) measurements revealed the properties of the as-prepared PCMC. The PCMC material exhibited outstanding thermal stability (Td10 = 660 °C and char yield = 75 wt%), a high BET surface area (1110 m2 g–1), high CO2 adsorption (5.40 mmol g–1 at 273 K), excellent capacitance (735 F g–1), and a capacitance retention of up to 95% after 2000 galvanostatic charge–discharge (GCD) cycles; these characteristics were excellent when compared with those of the corresponding microporous carbon (MPC) prepared through pyrolysis of the PA-BZ POP precursors with a ZIF-67 template at 500 °C.

show abstract

Combining naphthoxazines and benzoxazines for non-symmetric curable oxazines by one-pot synthesis

Cited by 25 publications

References 59 publications

Advanced Thermosets from Sulfur and Renewable Benzoxazine and Ionones via Inverse Vulcanization

Advanced Thermosets from Sulfur and Renewable Benzoxazine and Ionones via Inverse Vulcanization

Improvement of aldehyde‐functional polybenzoxazine processability and mechanical properties achieved by 5‐aminoindole/benzoxazine copolymerization

Microporous Carbon and Carbon/Metal Composite Materials Derived from Bio-Benzoxazine-Linked Precursor for CO2 Capture and Energy Storage Applications

Contact Info

Product

Resources

About