Synthesis of Water-Soluble, Intrinsically Flame-Retardant Benzoxazine Based on Renewable, Natural Resources

Against the general trend of developing hydrophobic benzoxazine resins, a novel water-soluble benzoxazine monomer with carbohydrate functionality (HP-fa) is synthesized. The synthesis and materials involved are all natural renewable raw materials that are designed to increase the concept of greenness and sustainability. The monomer was designed to improve compatibility with hydrophilic surfaces and environmental friendliness by the use of ethanol as a solvent. The structure of the synthesized monomer is verified using 1H NMR, 13C NMR, and Fourier transform infrared (FTIR) spectroscopy. The catalytic effect of hydroxyl groups in promoting polymerization is explored, which exhibits a heat of polymerization, ΔH, of 146.2 J/g and significantly low activation energies of polymerization of 25.9–97.2 kJ/mol. The differential scanning calorimetry (DSC) and thermogravimetric analyses (TGA) are employed to study the polymerization process and thermal stability. Two-dimensional nuclear magnetic resonance (2D NMR) spectroscopy is employed to elucidate the molecular structure and confirm the formation of the benzoxazine framework. The activation energy for the degradation of cross-linked HP-fa using the Flynn–Wall–Ozawa equation is determined. The flammability of the polymer derived from the synthesized monomer is determined using a microscale combustion calorimeter (MCC). The heat release capacity is observed to be very small at 25 J/(g·K), suggesting the intrinsic noncombustible nature of this polymer without added flame retardant.

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Publication Details

Journal
ACS Sustainable Chemistry & Engineering
Published
2025-03-07
DOI
https://doi.org/10.1021/acssuschemeng.4c10471
Citations
11
Primary Topic
Epoxy Resin Curing Processes
Type
article
Field-Weighted Citation Impact
7.85
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article

Synthesis of Water-Soluble, Intrinsically Flame-Retardant Benzoxazine Based on Renewable, Natural Resources

E.C. Heyman, Matthew Pearce, Hatsuo Ishida
11 citations
ACS Sustainable Chemistry & Engineering
Epoxy Resin Curing Processes
7.85
article

Synthesis of Water-Soluble, Intrinsically Flame-Retardant Benzoxazine Based on Renewable, Natural Resources

E.C. Heyman, Matthew Pearce, Hatsuo Ishida
article en
11 citations

Abstract

Against the general trend of developing hydrophobic benzoxazine resins, a novel water-soluble benzoxazine monomer with carbohydrate functionality (HP-fa) is synthesized. The synthesis and materials involved are all natural renewable raw materials that are designed to increase the concept of greenness and sustainability. The monomer was designed to improve compatibility with hydrophilic surfaces and environmental friendliness by the use of ethanol as a solvent. The structure of the synthesized monomer is verified using 1H NMR, 13C NMR, and Fourier transform infrared (FTIR) spectroscopy. The catalytic effect of hydroxyl groups in promoting polymerization is explored, which exhibits a heat of polymerization, ΔH, of 146.2 J/g and significantly low activation energies of polymerization of 25.9–97.2 kJ/mol. The differential scanning calorimetry (DSC) and thermogravimetric analyses (TGA) are employed to study the polymerization process and thermal stability. Two-dimensional nuclear magnetic resonance (2D NMR) spectroscopy is employed to elucidate the molecular structure and confirm the formation of the benzoxazine framework. The activation energy for the degradation of cross-linked HP-fa using the Flynn–Wall–Ozawa equation is determined. The flammability of the polymer derived from the synthesized monomer is determined using a microscale combustion calorimeter (MCC). The heat release capacity is observed to be very small at 25 J/(g·K), suggesting the intrinsic noncombustible nature of this polymer without added flame retardant.

ACS Sustainable Chemistry & EngineeringVol. 13(10)
Avery Dennison (United States) (US), Case Western Reserve University (US)
Responsible consumption and production
Openalex Percentile: Top 2%
Epoxy Resin Curing Processes
7.85
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