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Abstract:

Sesamol and furfurylamine are used to synthesize a novel benzoxazine monomer as part of the quest to develop greener benzoxazine monomers simultaneously fulfilling two Principles of Green Chemistry, the use of renewable feedstocks and safer solvents and auxiliaries. Respecting principle 5, the so-called preferred solvents (ethanol and ethyl acetate) are used in both the syntheses and purification processes. The chemical structure of the synthesized monomer is verified by proton and carbon nuclear magnetic resonance spectroscopy (1H and 13C NMR), 2D 1H-13C heteronuclear single quantum correlation (HSQC) spectroscopy, and Fourier transform infrared spectroscopy (FT-IR). The polymerization behavior of the monomer and the thermal stability of fully polymerized polybenzoxazine are studied by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). A thermally stable polymer has been obtained as shown by the 5% and 10% weight reduction temperature (Td5 and Td10) values of 374 and 419 °C, respectively, and a char yield of 64%, making this thermoset a promising candidate for fire-resistant applications. Copyright © 2018 American Chemical Society.

Registro:

Documento: Artículo
Título:Making Benzoxazines Greener: Design, Synthesis, and Polymerization of a Biobased Benzoxazine Fulfilling Two Principles of Green Chemistry
Autor:Salum, M.L.; Iguchi, D.; Arza, C.R.; Han, L.; Ishida, H.; Froimowicz, P.
Filiación:Department of Macromolecular Science and Engineering, Case Western Reserve University, 2100 Adelbert Road, Cleveland, OH 44106-7202, United States
Design and Chemistry of Macromolecules Group, Institute of Technology in Polymers and Nanotechnology (ITPN), UBA-CONICET, FIUBA, FADU, University of Buenos Aires, Ciudad Universitaria, Intendente Güiraldes s/n, Buenos Aires, 1428, Argentina
CIHIDECAR-CONICET, Departamento de Qui-mica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Intendente Guiraldes s/n, Pabellon II, 3er piso, Buenos Aires, 1428, Argentina
Palabras clave:Benzoxazine chemistry; Chemical design; Green solvents; Natural renewable resources; Differential scanning calorimetry; Fourier transform infrared spectroscopy; Monomers; Nuclear magnetic resonance spectroscopy; Organic solvents; Polymerization; Thermodynamic stability; Benzoxazine monomers; Fourier transform infra red (FTIR) spectroscopy; Heteronuclear single quantum correlations; Polymerization behavior; Purification process; Renewable feedstocks; Thermally stable polymers; Weight reduction; Thermogravimetric analysis
Año:2018
Volumen:6
Número:10
Página de inicio:13096
Página de fin:13106
DOI: http://dx.doi.org/10.1021/acssuschemeng.8b02641
Título revista:ACS Sustainable Chemistry and Engineering
Título revista abreviado:ACS Sustainable Chem. Eng.
ISSN:21680485
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_21680485_v6_n10_p13096_Salum

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Citas:

---------- APA ----------
Salum, M.L., Iguchi, D., Arza, C.R., Han, L., Ishida, H. & Froimowicz, P. (2018) . Making Benzoxazines Greener: Design, Synthesis, and Polymerization of a Biobased Benzoxazine Fulfilling Two Principles of Green Chemistry. ACS Sustainable Chemistry and Engineering, 6(10), 13096-13106.
http://dx.doi.org/10.1021/acssuschemeng.8b02641
---------- CHICAGO ----------
Salum, M.L., Iguchi, D., Arza, C.R., Han, L., Ishida, H., Froimowicz, P. "Making Benzoxazines Greener: Design, Synthesis, and Polymerization of a Biobased Benzoxazine Fulfilling Two Principles of Green Chemistry" . ACS Sustainable Chemistry and Engineering 6, no. 10 (2018) : 13096-13106.
http://dx.doi.org/10.1021/acssuschemeng.8b02641
---------- MLA ----------
Salum, M.L., Iguchi, D., Arza, C.R., Han, L., Ishida, H., Froimowicz, P. "Making Benzoxazines Greener: Design, Synthesis, and Polymerization of a Biobased Benzoxazine Fulfilling Two Principles of Green Chemistry" . ACS Sustainable Chemistry and Engineering, vol. 6, no. 10, 2018, pp. 13096-13106.
http://dx.doi.org/10.1021/acssuschemeng.8b02641
---------- VANCOUVER ----------
Salum, M.L., Iguchi, D., Arza, C.R., Han, L., Ishida, H., Froimowicz, P. Making Benzoxazines Greener: Design, Synthesis, and Polymerization of a Biobased Benzoxazine Fulfilling Two Principles of Green Chemistry. ACS Sustainable Chem. Eng. 2018;6(10):13096-13106.
http://dx.doi.org/10.1021/acssuschemeng.8b02641