Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable Resources

Autores
Zhang, Kan; Han, Mengchao; Liu, Yuqi; Froimowicz, Pablo
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A new fully biobased trioxazine benzoxazine is synthesized by reacting resveratrol, furfurylamine, and paraformaldehyde via the Mannich condensation reaction. The chemical structure of this biobenzoxazine is characterized by 1H and 13C nuclear magnetic resonance and Fourier transform infrared (FT-IR) spectroscopies. 1H-1H nuclear Overhauser effect spectroscopy is utilized to unambiguously identify the isomer obtained. Monomer polymerization is investigated by differential scanning calorimetry and in situ FT-IR. Thermal stability of the fully polymerized polybenzoxazine is evaluated by thermogravimetric analysis, and flammability is assessed by microscale combustion calorimetry. The biothermoset obtained shows high thermal stability and low flammability, Td10 of 403 °C and char yield of 64%, respectively, low heat release capacity (54 J/gK), and low total heat release (9.3 KJ/g), thus exhibiting self-extinguishing and nonignitable properties. Consequently, this new fully biobased trioxazine benzoxazine and its corresponding polybenzoxazine possess excellent processability and thermal properties, suggesting great potential toward high-performance and fire-resistant materials.
Fil: Zhang, Kan. Jiangsu University; China
Fil: Han, Mengchao. Jiangsu University; China
Fil: Liu, Yuqi. Jiangsu University; China
Fil: Froimowicz, Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Tecnología en Polímeros y Nanotecnología. Universidad de Buenos Aires. Facultad de Ingeniería. Instituto de Tecnología en Polímeros y Nanotecnología; Argentina
Materia
BENZOXAZINE
RESVERATROL
NATURAL RENEWABLE RESOURCES
HIGH PERFORMANCE
CHEMICAL DESIGN
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/121384
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/121384
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable ResourcesZhang, KanHan, MengchaoLiu, YuqiFroimowicz, PabloBENZOXAZINERESVERATROLNATURAL RENEWABLE RESOURCESHIGH PERFORMANCECHEMICAL DESIGNhttps://purl.org/becyt/ford/2.5https://purl.org/becyt/ford/2https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A new fully biobased trioxazine benzoxazine is synthesized by reacting resveratrol, furfurylamine, and paraformaldehyde via the Mannich condensation reaction. The chemical structure of this biobenzoxazine is characterized by 1H and 13C nuclear magnetic resonance and Fourier transform infrared (FT-IR) spectroscopies. 1H-1H nuclear Overhauser effect spectroscopy is utilized to unambiguously identify the isomer obtained. Monomer polymerization is investigated by differential scanning calorimetry and in situ FT-IR. Thermal stability of the fully polymerized polybenzoxazine is evaluated by thermogravimetric analysis, and flammability is assessed by microscale combustion calorimetry. The biothermoset obtained shows high thermal stability and low flammability, Td10 of 403 °C and char yield of 64%, respectively, low heat release capacity (54 J/gK), and low total heat release (9.3 KJ/g), thus exhibiting self-extinguishing and nonignitable properties. Consequently, this new fully biobased trioxazine benzoxazine and its corresponding polybenzoxazine possess excellent processability and thermal properties, suggesting great potential toward high-performance and fire-resistant materials.Fil: Zhang, Kan. Jiangsu University; ChinaFil: Han, Mengchao. Jiangsu University; ChinaFil: Liu, Yuqi. Jiangsu University; ChinaFil: Froimowicz, Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Tecnología en Polímeros y Nanotecnología. Universidad de Buenos Aires. Facultad de Ingeniería. Instituto de Tecnología en Polímeros y Nanotecnología; ArgentinaAmerican Chemical Society Inc2019-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/121384Zhang, Kan; Han, Mengchao; Liu, Yuqi; Froimowicz, Pablo; Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable Resources; American Chemical Society Inc; ACS Sustainable Chemistry and Engineering; 7; 10; 5-2019; 9399-94072168-0485CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acssuschemeng.9b00603info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acssuschemeng.9b00603info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:58:39Zoai:ri.conicet.gov.ar:11336/121384instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:58:39.39CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable Resources
title Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable Resources
spellingShingle Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable Resources
Zhang, Kan
BENZOXAZINE
RESVERATROL
NATURAL RENEWABLE RESOURCES
HIGH PERFORMANCE
CHEMICAL DESIGN
title_short Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable Resources
title_full Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable Resources
title_fullStr Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable Resources
title_full_unstemmed Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable Resources
title_sort Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable Resources
dc.creator.none.fl_str_mv Zhang, Kan
Han, Mengchao
Liu, Yuqi
Froimowicz, Pablo
author Zhang, Kan
author_facet Zhang, Kan
Han, Mengchao
Liu, Yuqi
Froimowicz, Pablo
author_role author
author2 Han, Mengchao
Liu, Yuqi
Froimowicz, Pablo
author2_role author
author
author
dc.subject.none.fl_str_mv BENZOXAZINE
RESVERATROL
NATURAL RENEWABLE RESOURCES
HIGH PERFORMANCE
CHEMICAL DESIGN
topic BENZOXAZINE
RESVERATROL
NATURAL RENEWABLE RESOURCES
HIGH PERFORMANCE
CHEMICAL DESIGN
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.5
https://purl.org/becyt/ford/2
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A new fully biobased trioxazine benzoxazine is synthesized by reacting resveratrol, furfurylamine, and paraformaldehyde via the Mannich condensation reaction. The chemical structure of this biobenzoxazine is characterized by 1H and 13C nuclear magnetic resonance and Fourier transform infrared (FT-IR) spectroscopies. 1H-1H nuclear Overhauser effect spectroscopy is utilized to unambiguously identify the isomer obtained. Monomer polymerization is investigated by differential scanning calorimetry and in situ FT-IR. Thermal stability of the fully polymerized polybenzoxazine is evaluated by thermogravimetric analysis, and flammability is assessed by microscale combustion calorimetry. The biothermoset obtained shows high thermal stability and low flammability, Td10 of 403 °C and char yield of 64%, respectively, low heat release capacity (54 J/gK), and low total heat release (9.3 KJ/g), thus exhibiting self-extinguishing and nonignitable properties. Consequently, this new fully biobased trioxazine benzoxazine and its corresponding polybenzoxazine possess excellent processability and thermal properties, suggesting great potential toward high-performance and fire-resistant materials.
Fil: Zhang, Kan. Jiangsu University; China
Fil: Han, Mengchao. Jiangsu University; China
Fil: Liu, Yuqi. Jiangsu University; China
Fil: Froimowicz, Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Tecnología en Polímeros y Nanotecnología. Universidad de Buenos Aires. Facultad de Ingeniería. Instituto de Tecnología en Polímeros y Nanotecnología; Argentina
description A new fully biobased trioxazine benzoxazine is synthesized by reacting resveratrol, furfurylamine, and paraformaldehyde via the Mannich condensation reaction. The chemical structure of this biobenzoxazine is characterized by 1H and 13C nuclear magnetic resonance and Fourier transform infrared (FT-IR) spectroscopies. 1H-1H nuclear Overhauser effect spectroscopy is utilized to unambiguously identify the isomer obtained. Monomer polymerization is investigated by differential scanning calorimetry and in situ FT-IR. Thermal stability of the fully polymerized polybenzoxazine is evaluated by thermogravimetric analysis, and flammability is assessed by microscale combustion calorimetry. The biothermoset obtained shows high thermal stability and low flammability, Td10 of 403 °C and char yield of 64%, respectively, low heat release capacity (54 J/gK), and low total heat release (9.3 KJ/g), thus exhibiting self-extinguishing and nonignitable properties. Consequently, this new fully biobased trioxazine benzoxazine and its corresponding polybenzoxazine possess excellent processability and thermal properties, suggesting great potential toward high-performance and fire-resistant materials.
publishDate 2019
dc.date.none.fl_str_mv 2019-05
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/121384
Zhang, Kan; Han, Mengchao; Liu, Yuqi; Froimowicz, Pablo; Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable Resources; American Chemical Society Inc; ACS Sustainable Chemistry and Engineering; 7; 10; 5-2019; 9399-9407
2168-0485
CONICET Digital
CONICET
url http://hdl.handle.net/11336/121384
identifier_str_mv Zhang, Kan; Han, Mengchao; Liu, Yuqi; Froimowicz, Pablo; Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable Resources; American Chemical Society Inc; ACS Sustainable Chemistry and Engineering; 7; 10; 5-2019; 9399-9407
2168-0485
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/acssuschemeng.9b00603
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acssuschemeng.9b00603
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society Inc
publisher.none.fl_str_mv American Chemical Society Inc
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1842269533092446208
score 13.13397

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