Role of magnolol embedded fully bio-based benzoxazines for hydrophobic, anti-microbial and anti-corrosion applications

Madesh, Priyanka; Krishnasamy, Balaji; Arumugam, Hariharan; Muthukaruppan, Alagar

doi:10.1039/d3nj05576k

New J. Chem.

2024

DOI: 10.1039/d3nj05576k

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Role of magnolol embedded fully bio-based benzoxazines for hydrophobic, anti-microbial and anti-corrosion applications

Priyanka Madesh,

Balaji Krishnasamy,

Hariharan Arumugam

et al.

Abstract: To minimize the possible usage of petroleum resources in the field of production of benzoxazines, the sustainable biological monomer magnolol has been utilized to synthesize bio-polybenzoxazines. Magnolol based bio-thermosetting benzoxazines...

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Cited by 7 publications

References 53 publications

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Synthesis and Polymerization of the Bio‐Benzoxazine Derived from Resveratrol and Thiophenemethylamine and Properties of its Polymer

Zhong,

Yin,

Sun

et al. 2024

Macro Chemistry & Physics

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Resveratrol and 2‐thiophenemethylamine have been employed in the synthesis of a novel tri‐functional benzoxazine (RES‐th) to develop the bio‐benzoxazine monomer. The chemical structure of the synthesized monomer is confirmed by various characterization technics. The polymerization behavior is monitored by in situ Fourier transform infrared spectroscopy (FTIR) and differential scanning calorimetry (DSC). The in situ FTIR results reveal distinct reaction mechanisms for the three oxazine rings presented in RES‐th, with both ether and phenolic Mannich bridge structures observed in the products. The activation energy values of RES‐th are calculated to be 119.05, 120.97, and 119.44 kJ mol−1 by Kissinger, Ozawa, and Starink methods, respectively, which are all based on the heat flow curves at various heating temperatures. The thermal stability and flame retardancy of the resulting polybenzoxazine (poly(RES‐th)) are investigated by thermogravimetric analysis (TGA) and microscale combustion calorimeter (MCC). The values of Td5 and Td10 of polybenzoxazine are found to be 356 °C and 399 °C, respectively, with a char yield of 66.3% at 800 °C. The prepared polybenzoxazine also demonstrates nonflammability characteristics with the values of heat release capacity (HRC) and total heat release rate (THR) of 18.65 J (g K)−1 and 2.69 kJ g−1, respectively. These findings suggest that the thermoset, poly(RES‐th), is a promising candidate for fire‐resistant applications.

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Synthesis and Polymerization of the Bio‐Benzoxazine Derived from Resveratrol and Thiophenemethylamine and Properties of its Polymer

Zhong,

Yin,

Sun

et al. 2024

Macro Chemistry & Physics

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Exploring the Potential of Bifunctional Polybenzoxazines Containing Schiff Bases for Superhydrophobic and Anticorrosion Properties: A Comprehensive Study on Synthesis and Characterization

Madesh,

Krishnasamy,

Kumarasamy

et al. 2024

Polymers for Advanced Techs

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Two series of bifunctional benzoxazines (HC‐benz and HA‐benz) containing Schiff bases (HC and HA) were synthesized through Mannich condensation. The structural confirmation of the Schiff base containing hydroxyl derivatives and benzoxazines was carried out using ATR‐FTIR, HRMS, and 1H‐NMR spectroscopic techniques. The cure behavior and thermal stability were studied using DSC and TGA, respectively. Among the different benzoxazines studied, the HC‐jfm and HA‐jfm benzoxazines exhibited the lowest curing temperature of 216°C and 211°C, respectively. Both poly(HC‐dde) and poly(HA‐dde) showed higher char yield value of 41% at 850°C. The values of LOI and heat resistance index calculated from TGA data infer that these benzoxazines in particular poly(HC‐dde) and poly(HA‐dde) can be conveniently used for self‐extinguishing and heat‐resistant applications which was proved by achieving V0 rating during vertical flammability test. Results from EIS studies showed that poly(HC‐jfm) and poly(HA‐jfm) exhibited corrosion protection efficiency of 99.19% and 99.99%. The value of water contact angle results suggested that all the synthesized polybenzoxazines are hydrophobic in nature, whereas the poly(HC‐ddm) and poly(HA‐ddm) revealed the superhydrophobic behavior with values of 149o and 159o, respectively. The cotton fabric coated with polybenzoxazine exhibits excellent resistance to UV and chemicals. Data from different studies infer that these benzoxazines can be used in the form of coatings for thermally stable, anticorrosive, and superhydrophobic high‐performance applications.

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Modified guaiacol‐based benzoxazines for optical, aggregation‐induced emission and corrosion‐resistant coating applications

Saravanamuthu,

Khaja Najimudeen,

Balaji

et al. 2024

Polymer International

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Two new kinds of modified bifunctional and trifunctional guaiacol, namely 4,4′‐(bis(4‐fluorophenyl)methylene)bis(2‐methoxyphenol) (BBM) and 4,4′‐((2‐hydroxy‐4‐methoxyphenyl)(phenyl)methylene)bis(2‐methoxyphenol) (HBM), were synthesized using guaiacol with respective keto derivatives under appropriate experimental conditions. Two series of benzoxazines were developed with BBM and HBM using various amines (dodecylamine (dda), octadecylamine (oda), furfurylamine (ffa), aniline (a) and 4‐fluoroaniline (fa)) with paraformaldehyde through Mannich condensation with a view to utilize them for anticorrosive and optical resistant coating applications. The molecular structures of the synthesized precursors and benzoxazine monomers were characterized using appropriate analytical techniques. The polymerization temperature of the benzoxazines was assessed using differential scanning calorimetry. Among the benzoxazine monomers synthesized, the monomer HBM‐fa exhibits the lowest curing temperature (217 °C). Data obtained from thermogravimetric analysis indicated that the polybenzoxazines poly(BBM‐ffa) and poly(HBM‐ffa) possess higher thermal stability (455 and 425 °C) and higher char yield (54% and 60%) than the other polybenzoxazines. In both series, octadecylamine‐based polybenzoxazines (BBM‐oda and HBM‐oda) exhibited the highest values of water contact angle of 148° and 149° respectively. Additionally, the benzoxazines showed aggregation‐induced emission properties during fluorescence studies. Morphological analyses using different analytical techniques on selected polybenzoxazines were carried out before and after the corrosion process. Results from corrosion studies, i.e. Tafel and Nyquist plots, implied that the polybenzoxazines can be used as effective coating material to protect mild steels from corrosion. Data from different studies suggest that the developed benzoxazines can be used in the form of optical and anticorrosion coatings under thermally harsh and moist environments. © 2024 Society of Chemical Industry.

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Role of magnolol embedded fully bio-based benzoxazines for hydrophobic, anti-microbial and anti-corrosion applications

Abstract: To minimize the possible usage of petroleum resources in the field of production of benzoxazines, the sustainable biological monomer magnolol has been utilized to synthesize bio-polybenzoxazines. Magnolol based bio-thermosetting benzoxazines...

Cited by 7 publications

References 53 publications

Synthesis and Polymerization of the Bio‐Benzoxazine Derived from Resveratrol and Thiophenemethylamine and Properties of its Polymer

Synthesis and Polymerization of the Bio‐Benzoxazine Derived from Resveratrol and Thiophenemethylamine and Properties of its Polymer

Exploring the Potential of Bifunctional Polybenzoxazines Containing Schiff Bases for Superhydrophobic and Anticorrosion Properties: A Comprehensive Study on Synthesis and Characterization

Modified guaiacol‐based benzoxazines for optical, aggregation‐induced emission and corrosion‐resistant coating applications

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