Diels–Alder Reaction as a Tool to Modify the Surface of Polymeric Microspheres

The study describes the synthesis of glycidyl methacrylate microspheres cross-linked with ethylene glycol dimethacrylate. With the use of suspension–emulsion polymerization, microspheres with different degrees of cross-linking were prepared. Their chemical modification involved several steps: at the...

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Main Authors: Marta Grochowicz, Przemysław Pączkowski, Barbara Gawdzik
Format: Article
Language:English
Published: SAGE Publishing 2015-08-01
Series:Adsorption Science & Technology
Online Access:https://doi.org/10.1260/0263-6174.33.6-8.677
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author Marta Grochowicz
Przemysław Pączkowski
Barbara Gawdzik
author_facet Marta Grochowicz
Przemysław Pączkowski
Barbara Gawdzik
author_sort Marta Grochowicz
collection DOAJ
description The study describes the synthesis of glycidyl methacrylate microspheres cross-linked with ethylene glycol dimethacrylate. With the use of suspension–emulsion polymerization, microspheres with different degrees of cross-linking were prepared. Their chemical modification involved several steps: at the beginning, the epoxide ring was opened using sodium cyclopentadienide; in the next step, materials with grafted cyclopentadiene fragments were then subjected to Diels–Alder reaction with maleic anhydride; in the last step, the anhydride groups were turned into carboxylic groups. To confirm the attachment of cyclopentadiene to the microspheres surface, the material obtained was treated with fluorescence marker N-(1-pyrene) maleimide. The resulting material has fluorescent properties in the UV wavelength of 366 nm. Moreover, to confirm the chemical structure of modified materials, attenuated total reflection-Fourier transform infrared spectroscopy analysis was performed. Thermal stability in inert atmosphere of prepared microspheres was determined. It was found that chemical modification of the microspheres surface improves their thermal resistance. On the basis of this study, it can be assumed that the Diels–Alder reaction is an expedient tool to obtain microspheres having carboxyl and hydroxyl groups, which can be an interesting option as stationary phases in chromatography.
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institution Kabale University
issn 0263-6174
2048-4038
language English
publishDate 2015-08-01
publisher SAGE Publishing
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series Adsorption Science & Technology
spelling doaj-art-7c3ab5dabb7345b2bd139729fe425b9e2025-01-03T01:25:17ZengSAGE PublishingAdsorption Science & Technology0263-61742048-40382015-08-013310.1260/0263-6174.33.6-8.677Diels–Alder Reaction as a Tool to Modify the Surface of Polymeric MicrospheresMarta GrochowiczPrzemysław PączkowskiBarbara GawdzikThe study describes the synthesis of glycidyl methacrylate microspheres cross-linked with ethylene glycol dimethacrylate. With the use of suspension–emulsion polymerization, microspheres with different degrees of cross-linking were prepared. Their chemical modification involved several steps: at the beginning, the epoxide ring was opened using sodium cyclopentadienide; in the next step, materials with grafted cyclopentadiene fragments were then subjected to Diels–Alder reaction with maleic anhydride; in the last step, the anhydride groups were turned into carboxylic groups. To confirm the attachment of cyclopentadiene to the microspheres surface, the material obtained was treated with fluorescence marker N-(1-pyrene) maleimide. The resulting material has fluorescent properties in the UV wavelength of 366 nm. Moreover, to confirm the chemical structure of modified materials, attenuated total reflection-Fourier transform infrared spectroscopy analysis was performed. Thermal stability in inert atmosphere of prepared microspheres was determined. It was found that chemical modification of the microspheres surface improves their thermal resistance. On the basis of this study, it can be assumed that the Diels–Alder reaction is an expedient tool to obtain microspheres having carboxyl and hydroxyl groups, which can be an interesting option as stationary phases in chromatography.https://doi.org/10.1260/0263-6174.33.6-8.677
spellingShingle Marta Grochowicz
Przemysław Pączkowski
Barbara Gawdzik
Diels–Alder Reaction as a Tool to Modify the Surface of Polymeric Microspheres
Adsorption Science & Technology
title Diels–Alder Reaction as a Tool to Modify the Surface of Polymeric Microspheres
title_full Diels–Alder Reaction as a Tool to Modify the Surface of Polymeric Microspheres
title_fullStr Diels–Alder Reaction as a Tool to Modify the Surface of Polymeric Microspheres
title_full_unstemmed Diels–Alder Reaction as a Tool to Modify the Surface of Polymeric Microspheres
title_short Diels–Alder Reaction as a Tool to Modify the Surface of Polymeric Microspheres
title_sort diels alder reaction as a tool to modify the surface of polymeric microspheres
url https://doi.org/10.1260/0263-6174.33.6-8.677
work_keys_str_mv AT martagrochowicz dielsalderreactionasatooltomodifythesurfaceofpolymericmicrospheres
AT przemysławpaczkowski dielsalderreactionasatooltomodifythesurfaceofpolymericmicrospheres
AT barbaragawdzik dielsalderreactionasatooltomodifythesurfaceofpolymericmicrospheres