DSpace at VNU: Efficient microencapsulation of a liquid isocyanate with in situ shell functionalization

Polymer Chemistry View Article Online View Journal Accepted Manuscript This article can be cited before page numbers have been issued, to this please use: L Nguyen, X Hillewaere, R Teixeira, O van den Berg and F Du Prez, Polym Chem., 2014, DOI: 10.1039/C4PY01448K This is an Accepted Manuscript, which has been through the Royal Society of Chemistry peer review process and has been accepted for publication Accepted Manuscripts are published online shortly after acceptance, before technical editing, formatting and proof reading Using this free service, authors can make their results available to the community, in citable form, before we publish the edited article We will replace this Accepted Manuscript with the edited and formatted Advance Article as soon as it is available You can find more information about Accepted Manuscripts in the Information for Authors Please note that technical editing may introduce minor changes to the text and/or graphics, which may alter content The journal’s standard Terms & Conditions and the Ethical guidelines still apply In no event shall the Royal Society of Chemistry be held responsible for any errors or omissions in this Accepted Manuscript or any consequences arising from the use of any information it contains www.rsc.org/polymers Page of 28 Polymer Chemistry View Article Online DOI: 10.1039/C4PY01448K Efficient microencapsulation of a liquid isocyanate with in situ shell functionalization Berg,† Filip E Du Prez*,† † Department of Organic and Macromolecular Chemistry, Polymer Chemistry Research group, Ghent University, Krijgslaan 281 S4, 9000 Gent, and SIM vzw, technologiepark 935, 9052 Zwijnaarde, Belgium ‡ Department of Polymer Materials, Faculty of Materials Technology, Ho Chi Minh City University of Technology−Vietnam National University, Ly Thuong Kiet 268, District 10, Ho Chi Minh City, Vietnam ABSTRACT: We report on a one-pot, facile approach for the encapsulation of the liquid hexamethylene diisocyanate isocyanurate trimer in polyurea microcapsules formed via the oil-in-water interfacial reaction of an uretonimine-modified diphenyl methane diisocyanate trimer with triaminopyrimidine, with in situ shell functionalization/modification using different types of hydrophobic agents Remarkably, the use of hexamethylenedisilazane resulted in microcapsules of about 70 µm in diameter, with a smooth outer surface and a high isocyanate core content up to 85 wt% as determined by quantitative online FT-IR analysis of the extracted core On the other hand, the use of an alkylamine, fluorinated aromatic amine and/or perfluoride amine provided microcapsules of approximately 100 to 150 µm in diameter containing around 65-75 wt% of the isocyanate core content, with the outer shell surface bearing pendant hydrophobic groups as confirmed by SEM-EDX The effects of the functionalizing compound on the microcapsule properties such as shell morphology, size distribution and stability were assessed After one day immersion in water, the initial isocyanate content of the microcapsules with a non-functionalized shell dropped rapidly from 49 to 15 wt%, whereas the ones with the modified shell structure maintained their core content, suggesting a significantly enhanced microcapsule stability Polymer Chemistry Accepted Manuscript Published on 11 November 2014 Downloaded by University of Chicago on 13/11/2014 09:46:00 Le-Thu T Nguyen,†,‡ Xander K D Hillewaere,† Roberto F A Teixeira,† Otto van den ... determined by quantitative online FT-IR analysis of the extracted core On the other hand, the use of an alkylamine, fluorinated aromatic amine and/or perfluoride amine provided microcapsules of approximately... oil -in- water interfacial reaction of an uretonimine-modified diphenyl methane diisocyanate trimer with triaminopyrimidine, with in situ shell functionalization/ modification using different types of hydrophobic... Vietnam ABSTRACT: We report on a one-pot, facile approach for the encapsulation of the liquid hexamethylene diisocyanate isocyanurate trimer in polyurea microcapsules formed via the oil -in- water interfacial