Preparation of robust polyamide microcapsules by interfacial polycondensation of p-phenylenediamine and sebacoyl chloride and plasticization with oleic acid

ABSTRACT

Microcapsules produced by interfacial polycondensation of p-phenylenediamine (PPD) and sebacoyl chloride (SC) were studied. The products were characterized in terms of morphology, mean diameter and effectiveness of dodecane encapsulation. The use of Tween 20 as dispersion stabilizer, in comparison with polyvinyl alcohol (PVA), reduced considerably the mean diameter of the microcapsules and originated smoother wall surfaces. When compared to ethylenediamine (EDA), microcapsules produced with PPD monomer were more rigid and brittle, prone to fracture during processing and ineffective retention of the core liquid. The use of diethylenetriamine (DETA) cross-linker in combination with PPD did not decrease capsule fragility. On the other hand, addition of a small fraction of oleic acid to the organic phase remarkably improved wall toughness and lead to successful encapsulation of the core-oil. Oleic acid is believed to act as a plasticizer. Its incorporation in the polymeric wall was demonstrated by FTIR and ¹H-NMR.

• Fragility
• interfacial polymerization
• mechanical stability
• microencapsulation
• smooth surface
• surfactant

Declaration of interest

This work was funded by FEDER funds through the Operational Programme for Competitiveness Factors (COMPETE), ON.2 – O Novo Norte – North Portugal Regional Operational Programme and National Funds through Foundation for Science and Technology (FCT) under the projects: PEst-C/EQB/UI0511, NORTE-07-0124-FEDER-000026 – RL1_ Energy and PTDC/CTM-NAN/119979/2010. The Bruker Avance III 400 spectrometer is part of the National NMR network and was purchased under the framework of the National Programme for Scientific Re-equipment, REDE/1517/RMN/2005, with funds from POCI 2010 (FEDER) and (FCT). Joana R. Góis acknowledges FCT-MCTES for her PhD scholarship (SFRH/BD/69635/2010).