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Reaction routes with glycidyl methacrylate for the incorporation of oleic acid in amphiphilic block copolymers

2025Journal article Open access
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datacite.subject.fosEngenharia e Tecnologia::Engenharia Química
datacite.subject.fosEngenharia e Tecnologia::Nanotecnologia
datacite.subject.sdg03:Saúde de Qualidade
datacite.subject.sdg09:Indústria, Inovação e Infraestruturas
dc.contributor.authorGomes, Catarina
dc.contributor.authorCosta, Mário Rui
dc.contributor.authorDias, Rolando
dc.date.accessioned2025-11-07T15:18:28Z
dc.date.available2025-11-07T15:18:28Z
dc.date.issued2025
dc.description.abstractThis research focused on assessing different reaction routes for synthesizing amphiphilic block copolymers, with the hydrophobic part built using glycidyl methacrylate and oleic acid and the hydrophilic segment made from 2(dimethylamino)ethyl methacrylate. The main objectives of this study were to identify reaction routes leading to low-impact branching and/or crosslinking mechanisms involving epoxides and oleic acid, and to synthesize p (GMA-OA)-b-p(DMAEMA) copolymers in a simple and scalable manner. Block copolymer synthesis was considered using both ATRP and RAFT polymerization. The reaction route involving the synthesis of methacrylated oleic acid proved problematic, whereas higher synthesis efficiency was achieved when the glycidyl methacrylate moieties were modified with oleic acid after polymerization. It was found that working with DMSO solvent and a stoichiometric excess of oleic acid was particularly important for reducing branching/crosslinking. FTIR and GPC analyses were used to assess the progress of the chemical composition and molecular architecture of the intermediate homo- and co-polymers, and to demonstrate the successful production of the intended p(GMA-OA)-b-p(DMAEMA) materials. The synthesized block copolymers were used for encapsulating and delivering oleanolic acid considering solid polymer dispersions and aqueous particle dispersions. SEM and TEM analysis demonstrate the ability of the p (GMA-OA)-b-p(DMAEMA) copolymers to self-assemble in an aqueous environment and well-defined spherical aggregates were observed, for example with size up to 100 nm in size with an external shell around 5-8 nm thick. A high loading capacity for oleanolic acid was measured, with a range of up to 0.17 mg/mL in aqueous particle dispersions. The dynamics of oleanolic acid release was measured under different conditions, including changes in solvent composition, pH and temperature. The results demonstrate sustained release of the encapsulated oleanolic acid and transitions induced by pH/temperature changes.eng
dc.description.sponsorshipCatarina Gomes acknowledges to FCT for the PhD scholarship 2020.06057.BD. Rolando Dias is grateful to the Foundation for Science and Technology (FCT, Portugal) for financial support through national funds FCT/MCTES (PIDDAC) to CIMO (UIDB/00690/2020 and UIDP/00690/2020) and SusTEC (LA/P/0007/2020). Mário Rui Costa acknowledges the support by LA/P/0045/2020 (ALiCE), UIDB/50020/2020 and UIDP/50020/2020 (LSRE-LCM), funded by national funds through FCT/MCTES (PIDDAC).
dc.identifier.citationGomes, Catarina; Costa, Mário Rui; Dias, Rolando (2025). Reaction routes with glycidyl methacrylate for the incorporation of oleic acid in amphiphilic block copolymers. Reactive and Functional Polymers. ISSN 1381-5148. 217, p. 1-16
dc.identifier.doi10.1016/j.reactfunctpolym.2025.106492
dc.identifier.issn1381-5148
dc.identifier.urihttp://hdl.handle.net/10198/34999
dc.language.isoeng
dc.peerreviewedyes
dc.publisherElsevier
dc.relationMountain Research Center
dc.relationAssociate Laboratory for Sustainability and Tecnology in Mountain Regions
dc.relationALICE - Associate Laboratory in Chemical Engineering
dc.relationLaboratory of Separation and Reaction Engineering - Laboratory of Catalysis and Materials
dc.relation.ispartofReactive and Functional Polymers
dc.rights.urihttp://creativecommons.org/licenses/by-nc/4.0/
dc.subjectGlycidyl methacrylate
dc.subjectOleic acid
dc.subjectAmphiphilic block copolymers
dc.subjectSelf-assembly
dc.subjectEncapsulation
dc.titleReaction routes with glycidyl methacrylate for the incorporation of oleic acid in amphiphilic block copolymerseng
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleMountain Research Center
oaire.awardTitleAssociate Laboratory for Sustainability and Tecnology in Mountain Regions
oaire.awardTitleALICE - Associate Laboratory in Chemical Engineering
oaire.awardTitleLaboratory of Separation and Reaction Engineering - Laboratory of Catalysis and Materials
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F00690%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/LA%2FP%2F0007%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/LA%2FP%2F0045%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50020%2F2020/PT
oaire.citation.endPage16
oaire.citation.startPage1
oaire.citation.titleReactive & Functional Polymers
oaire.citation.volume217
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.versionhttp://purl.org/coar/version/c_970fb48d4fbd8a85
person.familyNameGomes
person.familyNameDias
person.givenNameCatarina
person.givenNameRolando
person.identifier.ciencia-id2B12-75A1-B8FB
person.identifier.ciencia-id8417-4D84-973B
person.identifier.orcid0000-0003-3396-3615
person.identifier.orcid0000-0001-7369-382X
person.identifier.ridM-8552-2013
person.identifier.scopus-author-id57190981477
person.identifier.scopus-author-id7102885104
project.funder.identifierhttp://doi.org/10.13039/501100001871
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project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
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