Issue 34, 2021

Polyvinyl alcohol modification with sustainable ketones

Abstract

A series of polyvinyl ketals was synthesized by the condensation of commercially available polyvinyl alcohol (PVA) and biobased ketones, raspberry ketone, zingerone, D-dihydrocarvone, and levulinic acid, as well as acetone, butanone, 3-pentanone, cyclopentanone, cyclohexanone, 3,3,5-trimethylcyclohexanone, along with the aldehyde furfural. Ketalization was confirmed and measured by 1H NMR, ranging from 15.3 to 69.2%. The number average molecular weights of the polyvinyl ketals ranged from 24 400 to 41 100 Da, according to the mass added by ketalization. The glass transition temperature (Tg) of PVA, 75 °C, increased through ketalization, reaching 78 °C to 127 °C or through acetalization with furfural, reaching 138 °C. Kinetic studies of polyvinyl acetone ketal (PV-A-K) formation showed the ketalization reaction neared equilibrium (69% ketalization) in 4 hours at 40 °C. During room temperature heterogeneous degradation studies, PV-A-K completely hydrolyzed in 1 day at pH = 2 or in 3 months at pH = 5; after 2 years in deionized water or seawater, ketalization diminished from 69% to 66% (3% hydrolysis). At 80 °C over 3 months, PV-A-K ketalization diminished to 5% (95% hydrolysis) in deionized water and to 1% (99% hydrolysis) in seawater. These studies suggest that polyvinyl ketals are suitable candidates for water-degradable packaging materials.

Graphical abstract: Polyvinyl alcohol modification with sustainable ketones

Supplementary files

Article information

Article type
Paper
Submitted
14 may 2021
Accepted
20 iyl 2021
First published
17 avq 2021

Polym. Chem., 2021,12, 4961-4973

Author version available

Polyvinyl alcohol modification with sustainable ketones

Y. Su, C. M. Coxwell, S. Shen and S. A. Miller, Polym. Chem., 2021, 12, 4961 DOI: 10.1039/D1PY00656H

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