Síntese, caracterização e cinética de polimerização de novas benzoxazinas a partir do Cardanol

Detalhes bibliográficos
Ano de defesa: 2019
Autor(a) principal: Pereira, Rita de Cássia Sousa
Orientador(a): Mazzetto, Selma Elaine
Banca de defesa: Não Informado pela instituição
Tipo de documento: Dissertação
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Não Informado pela instituição
Programa de Pós-Graduação: Não Informado pela instituição
Departamento: Não Informado pela instituição
País: Não Informado pela instituição
Palavras-chave em Português:
Link de acesso: http://www.repositorio.ufc.br/handle/riufc/41428
Resumo: Benzoxazines are a class of monomers which have aroused great interest in the scientific scenario, due regarding its excellent chemical, thermal and mechanical properties, characterizing itself as a great alternative for the development of new polymeric materials. This work aims to obtain two novel 2-substituted benzoxazines through a procedure carried out in three steps: (1) Functionalization of the cardanol, a monophenol present in the Cashew Nut Shell Liquid (CNSL), to obtain an ortho-formylated product; (2) Functionalized cardanol was combined with furfurylamine, an amine derived from furfural, obtained from lignocellulosic waste, to obtain an ortho-aminomethylphenol compound; (3) This product combined with different aldehydes (valeraldehyde and benzaldehyde), gives rise to novel monomers through a solvent-free procedure under microwave irradiation. The synthetic pathway was efficient to obtain the products, which had their chemical structures confirmed by Nuclear Magnetic Resonance Spectroscopy (1H-NMR and 13CNMR) and Fourier Transform Infrared Spectroscopy (FT-IR), with good yields and high purity. The thermal stability of the monomers was evaluated by Thermogravimetric Analysis (TGA) and kinetic polymerization behavior was studied by Differential Scanning Calorimetry (DSC), by applying Kissinger, Flynn-Wall-Ozawa and Crane methods to determine the activation energy (Ea) of the studied system. DSC thermograms showed that the synthesized monomers presented lower values of Ea and polymerization temperatures compared to the corresponding unsubstituted benzoxazine, in addition to a wide processing-window. The use of different aldehydes allowed to obtain monomers with high polymerization potential, which allows the addition of new functions to the resulting polymers, according to the applications perspectives.
id UFC-7_dff8c6203ab1d0f3348dcd21adf98db3
oai_identifier_str oai:repositorio.ufc.br:riufc/41428
network_acronym_str UFC-7
network_name_str Repositório Institucional da Universidade Federal do Ceará (UFC)
repository_id_str
spelling Pereira, Rita de Cássia SousaOliveira, Diego Lomonaco Vasconcelos deMazzetto, Selma Elaine2019-05-06T21:50:43Z2019-05-06T21:50:43Z2019PEREIRA, Rita de Cássia Sousa. Síntese, caracterização e cinética de polimerização de novas benzoxazinas a partir do Cardanol. 2019. 62 f. Dissertação (Mestrado em Química) – Universidade Federal do Ceará, Fortaleza, 2019.http://www.repositorio.ufc.br/handle/riufc/41428Benzoxazines are a class of monomers which have aroused great interest in the scientific scenario, due regarding its excellent chemical, thermal and mechanical properties, characterizing itself as a great alternative for the development of new polymeric materials. This work aims to obtain two novel 2-substituted benzoxazines through a procedure carried out in three steps: (1) Functionalization of the cardanol, a monophenol present in the Cashew Nut Shell Liquid (CNSL), to obtain an ortho-formylated product; (2) Functionalized cardanol was combined with furfurylamine, an amine derived from furfural, obtained from lignocellulosic waste, to obtain an ortho-aminomethylphenol compound; (3) This product combined with different aldehydes (valeraldehyde and benzaldehyde), gives rise to novel monomers through a solvent-free procedure under microwave irradiation. The synthetic pathway was efficient to obtain the products, which had their chemical structures confirmed by Nuclear Magnetic Resonance Spectroscopy (1H-NMR and 13CNMR) and Fourier Transform Infrared Spectroscopy (FT-IR), with good yields and high purity. The thermal stability of the monomers was evaluated by Thermogravimetric Analysis (TGA) and kinetic polymerization behavior was studied by Differential Scanning Calorimetry (DSC), by applying Kissinger, Flynn-Wall-Ozawa and Crane methods to determine the activation energy (Ea) of the studied system. DSC thermograms showed that the synthesized monomers presented lower values of Ea and polymerization temperatures compared to the corresponding unsubstituted benzoxazine, in addition to a wide processing-window. The use of different aldehydes allowed to obtain monomers with high polymerization potential, which allows the addition of new functions to the resulting polymers, according to the applications perspectives.As benzoxazinas são uma classe de monômeros que têm despertado grande interesse no cenário científico, por apresentarem excelentes propriedades químicas, térmicas e mecânicas, caracterizando-se como uma ótima alternativa para o desenvolvimento de novos materiais poliméricos. Este trabalho tem como objetivo obter duas novas benzoxazinas-2-substituídas, através de um procedimento desenvolvido em três etapas: (1) Funcionalização do cardanol, um monofenol presente no Líquido da Casca da Castanha de Caju (LCC), para obtenção de um produto orto-formilado; (2) O cardanol funcionalizado foi combinado com furfurilamina, uma amina derivada do furfural, obtido a partir de resíduos lignocelulósicos, para obtenção de um derivado orto-aminometilfenol; (3) Combinação do derivado obtido, com diferentes aldeídos (valeraldeído e benzaldeído), dando origem a novos monômeros através de um procedimento sem solvente, sob irradiação de micro-ondas. A sequência reacional mostrou-se eficiente para obtenção dos produtos, cujas estruturas químicas foram confirmadas através das técnicas espectroscópicas de Infravermelho com Transformada de Fourier (FT-IR) e Ressonância Magnética Nuclear de 1H e 13C, com bons rendimentos e elevada pureza. A estabilidade térmica dos monômeros foi avaliada por Análise Termogravimétrica (TGA) e a cinética do comportamento de polimerização foi estudada através de Calorimetria Exploratória Diferencial (DSC), aplicando os métodos de Kissinger, Flynn-Wall-Ozawa e Crane para determinação da energia de ativação. Os resultados dos termogramas de DSC mostraram que os produtos sintetizados apresentaram menores valores de Ea e de temperaturas de polimerização, quando comparados com a correspondente benzoxazina não substituída, além de uma ampla janela de processabilidade. O uso de diferentes aldeídos tornou possível a obtenção de monômeros com elevado potencial de polimerização, o que possibilita a adição de novas funções aos polímeros resultantes, de acordo com as perspectivas de aplicações.PolibenzoxazinasCinética de polimerizaçãoResíduos agroindustriaisSíntese, caracterização e cinética de polimerização de novas benzoxazinas a partir do CardanolSynthesis, characterization and polymerization kinetics of novel benzoxazines from Cardanolinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisporreponame:Repositório Institucional da Universidade Federal do Ceará (UFC)instname:Universidade Federal do Ceará (UFC)instacron:UFCinfo:eu-repo/semantics/openAccessORIGINAL2019_dis_rcspereira.pdf2019_dis_rcspereira.pdfapplication/pdf2357922http://repositorio.ufc.br/bitstream/riufc/41428/3/2019_dis_rcspereira.pdf8d999e9024ed98e320ec3a616558a2dcMD53LICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://repositorio.ufc.br/bitstream/riufc/41428/4/license.txt8a4605be74aa9ea9d79846c1fba20a33MD54riufc/414282020-06-19 11:19:49.135oai:repositorio.ufc.br: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Repositório InstitucionalPUBhttp://www.repositorio.ufc.br/ri-oai/requestbu@ufc.br || repositorio@ufc.bropendoar:2020-06-19T14:19:49Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)false
dc.title.pt_BR.fl_str_mv Síntese, caracterização e cinética de polimerização de novas benzoxazinas a partir do Cardanol
dc.title.en.pt_BR.fl_str_mv Synthesis, characterization and polymerization kinetics of novel benzoxazines from Cardanol
title Síntese, caracterização e cinética de polimerização de novas benzoxazinas a partir do Cardanol
spellingShingle Síntese, caracterização e cinética de polimerização de novas benzoxazinas a partir do Cardanol
Pereira, Rita de Cássia Sousa
Polibenzoxazinas
Cinética de polimerização
Resíduos agroindustriais
title_short Síntese, caracterização e cinética de polimerização de novas benzoxazinas a partir do Cardanol
title_full Síntese, caracterização e cinética de polimerização de novas benzoxazinas a partir do Cardanol
title_fullStr Síntese, caracterização e cinética de polimerização de novas benzoxazinas a partir do Cardanol
title_full_unstemmed Síntese, caracterização e cinética de polimerização de novas benzoxazinas a partir do Cardanol
title_sort Síntese, caracterização e cinética de polimerização de novas benzoxazinas a partir do Cardanol
author Pereira, Rita de Cássia Sousa
author_facet Pereira, Rita de Cássia Sousa
author_role author
dc.contributor.co-advisor.none.fl_str_mv Oliveira, Diego Lomonaco Vasconcelos de
dc.contributor.author.fl_str_mv Pereira, Rita de Cássia Sousa
dc.contributor.advisor1.fl_str_mv Mazzetto, Selma Elaine
contributor_str_mv Mazzetto, Selma Elaine
dc.subject.por.fl_str_mv Polibenzoxazinas
Cinética de polimerização
Resíduos agroindustriais
topic Polibenzoxazinas
Cinética de polimerização
Resíduos agroindustriais
description Benzoxazines are a class of monomers which have aroused great interest in the scientific scenario, due regarding its excellent chemical, thermal and mechanical properties, characterizing itself as a great alternative for the development of new polymeric materials. This work aims to obtain two novel 2-substituted benzoxazines through a procedure carried out in three steps: (1) Functionalization of the cardanol, a monophenol present in the Cashew Nut Shell Liquid (CNSL), to obtain an ortho-formylated product; (2) Functionalized cardanol was combined with furfurylamine, an amine derived from furfural, obtained from lignocellulosic waste, to obtain an ortho-aminomethylphenol compound; (3) This product combined with different aldehydes (valeraldehyde and benzaldehyde), gives rise to novel monomers through a solvent-free procedure under microwave irradiation. The synthetic pathway was efficient to obtain the products, which had their chemical structures confirmed by Nuclear Magnetic Resonance Spectroscopy (1H-NMR and 13CNMR) and Fourier Transform Infrared Spectroscopy (FT-IR), with good yields and high purity. The thermal stability of the monomers was evaluated by Thermogravimetric Analysis (TGA) and kinetic polymerization behavior was studied by Differential Scanning Calorimetry (DSC), by applying Kissinger, Flynn-Wall-Ozawa and Crane methods to determine the activation energy (Ea) of the studied system. DSC thermograms showed that the synthesized monomers presented lower values of Ea and polymerization temperatures compared to the corresponding unsubstituted benzoxazine, in addition to a wide processing-window. The use of different aldehydes allowed to obtain monomers with high polymerization potential, which allows the addition of new functions to the resulting polymers, according to the applications perspectives.
publishDate 2019
dc.date.accessioned.fl_str_mv 2019-05-06T21:50:43Z
dc.date.available.fl_str_mv 2019-05-06T21:50:43Z
dc.date.issued.fl_str_mv 2019
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
format masterThesis
status_str publishedVersion
dc.identifier.citation.fl_str_mv PEREIRA, Rita de Cássia Sousa. Síntese, caracterização e cinética de polimerização de novas benzoxazinas a partir do Cardanol. 2019. 62 f. Dissertação (Mestrado em Química) – Universidade Federal do Ceará, Fortaleza, 2019.
dc.identifier.uri.fl_str_mv http://www.repositorio.ufc.br/handle/riufc/41428
identifier_str_mv PEREIRA, Rita de Cássia Sousa. Síntese, caracterização e cinética de polimerização de novas benzoxazinas a partir do Cardanol. 2019. 62 f. Dissertação (Mestrado em Química) – Universidade Federal do Ceará, Fortaleza, 2019.
url http://www.repositorio.ufc.br/handle/riufc/41428
dc.language.iso.fl_str_mv por
language por
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.source.none.fl_str_mv reponame:Repositório Institucional da Universidade Federal do Ceará (UFC)
instname:Universidade Federal do Ceará (UFC)
instacron:UFC
instname_str Universidade Federal do Ceará (UFC)
instacron_str UFC
institution UFC
reponame_str Repositório Institucional da Universidade Federal do Ceará (UFC)
collection Repositório Institucional da Universidade Federal do Ceará (UFC)
bitstream.url.fl_str_mv http://repositorio.ufc.br/bitstream/riufc/41428/3/2019_dis_rcspereira.pdf
http://repositorio.ufc.br/bitstream/riufc/41428/4/license.txt
bitstream.checksum.fl_str_mv 8d999e9024ed98e320ec3a616558a2dc
8a4605be74aa9ea9d79846c1fba20a33
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
repository.name.fl_str_mv Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)
repository.mail.fl_str_mv bu@ufc.br || repositorio@ufc.br
_version_ 1847793294350745600