Biobased diglycidyl ether diphenolates: effect of the ester moiety on fragrance oil microencapsulation by interfacial polymerization

Wang, Xue
Amason, Anna Christina
Miceli, Rebecca T.
He, Peng
Lei, Yabin
Gabbard, Ron
Wieland, Julie Ann
Linhardt, Robert J.
Corr, David T.
Gross, Richard A.
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Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
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Xue Wang, Anna-Christina Amason, Rebecca T. Miceli, Peng He, Yabin Lei, Ron Gabbard, Julie Ann Wieland, Robert J. Linhardt, David T. Corr, Richard A. Gross, Biobased diglycidyl ether diphenolates: Effect of the ester moiety on fragrance oil microencapsulation by interfacial polymerization, Colloids and Surfaces A: Physicochemical and Engineering Aspects, Volume 648, 2022, 129243, ISSN 0927-7757,
Health risks are associated with capsule-forming synthetic chemicals such as formaldehyde, isocyanates, and bisphenol A (BPA). This work is focused on using safe biobased molecules to build capsule walls for oil encapsulation. Cellulose-derived diphenolic acid was converted into a series of diglycidyl ether n-alkyl diphenolates (DGEDP-esters). Interfacial polymerization of oil-soluble DGEDP-esters and water-soluble amine hardeners, hexamethylenediamine (HMDA) and chitosan oligosaccharide (COS), were used to build capsule walls. DGEDP-esters with small methyl and polar monomethyl ethylene glycol (DGEDP-ME and DGEDP-MG, respectively) are most reactive forming compact crosslinked capsules with high microencapsulation efficiency (EE of 97% and 94.3%) and good stability (oil leaking was ≤ 15.7% after acidification, and ≤ 64.2% after sonication). With increased hydrophobicity of the DGEDP ester moiety, deformed capsules with low EE (63 – 87%) and poor stability (oil leaking was ≥ 18.4% after acidification, and ≥ 81.8% after sonication) were obtained. Oil encapsulated with DGEDP-esters exhibits oil release of 0.5 – 8% at day 30 (45 °C and 11 kPa). The use of COS as the hardener yields capsules with EE (88.3 – 94%) and higher oil release (9–15% at day 30) compared to HMDA, but the acid stability was remarkably improved (oil leaking ≤ 3.7%). Cytotoxicity tests suggest that capsules formed with DGEDP-ME and HMDA or COS show very low cytotoxicity against human breast cancer cells and human fibroblasts cells (cell viability of 87–102% after 24 h exposure at capsule concentration of 2 mg/mL). These observations demonstrate that the structures of DGEDP epoxy monomers and amine hardeners have significant effects. Preferred DGEDP ester groups were methyl and mono-methoxy, and effective capsule formation was achieved using either HMDA or COS, the latter providing the advantage of being a readily renewable biobased multifunctional amine.
Colloids and Surfaces A: Physicochemical and Engineering Aspects, in press
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The Linhardt Research Labs.
The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
The Linhardt Research Labs Online Collection
Rensselaer Polytechnic Institute, Troy, NY
Colloids and Surfaces A: Physicochemical and Engineering Aspects