Biobased diglycidyl ether diphenolates: effect of the ester moiety on fragrance oil microencapsulation by interfacial polymerization
Authors
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.
ORCID
https://orcid.org/0000-0003-2219-5833
No Thumbnail Available
Other Contributors
Issue Date
2022-09-05
Keywords
Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
Degree
Terms of Use
In Copyright : this Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s). https://rightsstatements.org/page/InC/1.0/
Full Citation
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, https://doi.org/10.1016/j.colsurfa.2022.129243.
Abstract
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.
Description
Colloids and Surfaces A: Physicochemical and Engineering Aspects, in press
Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
Department
The Linhardt Research Labs.
The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
Publisher
Relationships
The Linhardt Research Labs Online Collection
Rensselaer Polytechnic Institute, Troy, NY
Colloids and Surfaces A: Physicochemical and Engineering Aspects
https://harc.rpi.edu/
Rensselaer Polytechnic Institute, Troy, NY
Colloids and Surfaces A: Physicochemical and Engineering Aspects
https://harc.rpi.edu/
Access
https://login.libproxy.rpi.edu/login?url=https://doi.org/10.1016/j.colsurfa.2022.129243