Síntese, caracterização e cinética de polimerização de novas benzoxazinas a partir do Cardanol
| Ano de defesa: | 2019 |
|---|---|
| Autor(a) principal: | |
| Orientador(a): | |
| Banca de defesa: | |
| Tipo de documento: | Dissertação |
| Tipo de acesso: | Acesso aberto |
| Idioma: | por |
| Instituição de defesa: |
Não Informado pela instituição
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| Programa de Pós-Graduação: |
Não Informado pela instituição
|
| Departamento: |
Não Informado pela instituição
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| 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. |
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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 |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/masterThesis |
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masterThesis |
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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. |
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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. |
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http://www.repositorio.ufc.br/handle/riufc/41428 |
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por |
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por |
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