Spectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazines

Detalhes bibliográficos
Ano de defesa: 2016
Autor(a) principal: Kotzebue, Lloyd Ryan Viana
Orientador(a): Oliveira, Diego Lomonaco Vasconcelos de
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:
LCC
ROP
Link de acesso: http://www.repositorio.ufc.br/handle/riufc/29042
Resumo: A new class of polymers that is gaining attention of industry and academia are the polybenzoxazines, which can be obtained after the thermal polymerization of their monomers, benzoxazines. Due to the great versatility of the synthesis of these monomers, which uses a phenolic compound and primary amine, it is possible to use renewable sources such as cardanol and the manipulation of the monomer and polymer properties. However, an unexplored area is the understanding of the type of starting material used with the synthesis and polymerization of benzoxazines. Therefore, the aim of this study was to investigate how different primary amines structures influence on the synthesis and polymerization of novel cardanol-based benzoxazines. The monomers were characterized and compared using NMR (1H and 13C), FT-IR, DSC and TGA. It was demonstrated how primary amines influence on the stability of the oxazine ring, which relates to the onset polymerization temperature (Te). Aniline-type benzoxazines provided higher Te than aliphatic ones. Knowing that elevate Te, around 230 to 295 oC, could degrade the long alkyl chain of cardanol, the use of catalysts was also evaluated, showing the innocuous MgCl2 as very promising catalyst. The polymerization of these monomers with MgCl2 (1%) were studied using FT-IR, DSC and GPC, showing that according to the polymerization behaviour of each benzoxazine, this approach can be applied successfully for a more effective synthesis of cardanol-based polybenzoxazines.
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spelling Kotzebue, Lloyd Ryan VianaOliveira, Diego Lomonaco Vasconcelos de2018-01-17T13:01:30Z2018-01-17T13:01:30Z2016KOTZEBUE, Lloyd Ryan Viana. Spectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazines. 2016. 76 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2016.http://www.repositorio.ufc.br/handle/riufc/29042A new class of polymers that is gaining attention of industry and academia are the polybenzoxazines, which can be obtained after the thermal polymerization of their monomers, benzoxazines. Due to the great versatility of the synthesis of these monomers, which uses a phenolic compound and primary amine, it is possible to use renewable sources such as cardanol and the manipulation of the monomer and polymer properties. However, an unexplored area is the understanding of the type of starting material used with the synthesis and polymerization of benzoxazines. Therefore, the aim of this study was to investigate how different primary amines structures influence on the synthesis and polymerization of novel cardanol-based benzoxazines. The monomers were characterized and compared using NMR (1H and 13C), FT-IR, DSC and TGA. It was demonstrated how primary amines influence on the stability of the oxazine ring, which relates to the onset polymerization temperature (Te). Aniline-type benzoxazines provided higher Te than aliphatic ones. Knowing that elevate Te, around 230 to 295 oC, could degrade the long alkyl chain of cardanol, the use of catalysts was also evaluated, showing the innocuous MgCl2 as very promising catalyst. The polymerization of these monomers with MgCl2 (1%) were studied using FT-IR, DSC and GPC, showing that according to the polymerization behaviour of each benzoxazine, this approach can be applied successfully for a more effective synthesis of cardanol-based polybenzoxazines.Uma nova classe de polímeros que vem chamado atenção da indústria e da academia são as polibenzoxazinas, que podem ser obtidos após a polimerização térmica do seus monômeros, as benzoxazinas. Devido à grande versatilidade de síntese destes monômeros, que utiliza um composto fenólico e amina primária, possibilita-se o uso de fontes renováveis como o cardanol e a manipulação das propriedades do monômero e do polímero. Porém uma área pouco explorada é a compreensão da relação do tipo do material de partida utilizado com a síntese e polimerização das benzoxazinas. Desta forma, o objetivo deste estudo foi investigar como diferentes estruturas de aminas primárias influenciam na síntese e polimerização de novas benzoxazinas à base de cardanol. Os monômeros foram caracterizados e comparados utilizando RMN (1H e 13C), FT-IR, DSC e TGA. Demonstraram-se como aminas primárias influenciam na estabilidade do anel de oxazina, que se relaciona com a temperatura onset de polimerização (Te). Benzoxazinas do tipo anilina proporcionam maior Te do que as alifáticas. Sabendo que a alta Te, cerca de 230 a 295 °C, poderia degradar a longa cadeia alquílica do cardanol, foram avaliados também a utilização de catalisadores, demonstrando o inócuo MgCl2 ser um catalisador bastante promissor. A polimerização destes monômeros com MgCl2 (1%) foi estudada utilizando FT-IR, DSC e GPC, mostrando que, de acordo com o comportamento de polimerização de cada benzoxazina, esta abordagem pode ser aplicada para uma melhor síntese de polibenzoxazinas à base de cardanol.LCCCardanolPolimerização térmicaROPSpectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazinesSpectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazinesinfo: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/openAccessLICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://repositorio.ufc.br/bitstream/riufc/29042/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52ORIGINAL2016_dis_lrvkotzebue.pdf2016_dis_lrvkotzebue.pdfapplication/pdf4600879http://repositorio.ufc.br/bitstream/riufc/29042/3/2016_dis_lrvkotzebue.pdf3283295e0668b20be71be5739139bc5aMD53riufc/290422020-06-19 10:01:28.093oai:repositorio.ufc.br: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Repositório InstitucionalPUBhttp://www.repositorio.ufc.br/ri-oai/requestbu@ufc.br || repositorio@ufc.bropendoar:2020-06-19T13:01:28Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)false
dc.title.pt_BR.fl_str_mv Spectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazines
dc.title.en.pt_BR.fl_str_mv Spectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazines
title Spectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazines
spellingShingle Spectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazines
Kotzebue, Lloyd Ryan Viana
LCC
Cardanol
Polimerização térmica
ROP
title_short Spectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazines
title_full Spectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazines
title_fullStr Spectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazines
title_full_unstemmed Spectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazines
title_sort Spectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazines
author Kotzebue, Lloyd Ryan Viana
author_facet Kotzebue, Lloyd Ryan Viana
author_role author
dc.contributor.author.fl_str_mv Kotzebue, Lloyd Ryan Viana
dc.contributor.advisor1.fl_str_mv Oliveira, Diego Lomonaco Vasconcelos de
contributor_str_mv Oliveira, Diego Lomonaco Vasconcelos de
dc.subject.por.fl_str_mv LCC
Cardanol
Polimerização térmica
ROP
topic LCC
Cardanol
Polimerização térmica
ROP
description A new class of polymers that is gaining attention of industry and academia are the polybenzoxazines, which can be obtained after the thermal polymerization of their monomers, benzoxazines. Due to the great versatility of the synthesis of these monomers, which uses a phenolic compound and primary amine, it is possible to use renewable sources such as cardanol and the manipulation of the monomer and polymer properties. However, an unexplored area is the understanding of the type of starting material used with the synthesis and polymerization of benzoxazines. Therefore, the aim of this study was to investigate how different primary amines structures influence on the synthesis and polymerization of novel cardanol-based benzoxazines. The monomers were characterized and compared using NMR (1H and 13C), FT-IR, DSC and TGA. It was demonstrated how primary amines influence on the stability of the oxazine ring, which relates to the onset polymerization temperature (Te). Aniline-type benzoxazines provided higher Te than aliphatic ones. Knowing that elevate Te, around 230 to 295 oC, could degrade the long alkyl chain of cardanol, the use of catalysts was also evaluated, showing the innocuous MgCl2 as very promising catalyst. The polymerization of these monomers with MgCl2 (1%) were studied using FT-IR, DSC and GPC, showing that according to the polymerization behaviour of each benzoxazine, this approach can be applied successfully for a more effective synthesis of cardanol-based polybenzoxazines.
publishDate 2016
dc.date.issued.fl_str_mv 2016
dc.date.accessioned.fl_str_mv 2018-01-17T13:01:30Z
dc.date.available.fl_str_mv 2018-01-17T13:01:30Z
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 KOTZEBUE, Lloyd Ryan Viana. Spectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazines. 2016. 76 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2016.
dc.identifier.uri.fl_str_mv http://www.repositorio.ufc.br/handle/riufc/29042
identifier_str_mv KOTZEBUE, Lloyd Ryan Viana. Spectral and thermal studies on the synthesis and oligomerization of novel cardanol-based benzoxazines. 2016. 76 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2016.
url http://www.repositorio.ufc.br/handle/riufc/29042
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