Issue 34, 2017

Sustainable polyvinyl acetals from bioaromatic aldehydes

Abstract

A series of polyvinyl aromatic acetals was obtained from the condesation of commercially available polyvinyl alcohol (PVA) and sustainable aromatic aldehydes: 4-hydroxybenzaldehyde, vanillin, syringaldehyde, ethylvanillin, ortho-vanillin, isovanillin, salicylaldehyde, ortho-anisaldehyde, para-anisaldehyde, benzaldehyde, cinnamaldehyde, cuminaldehyde, and hydroxymethylfurfural. The degree of acetalization was determined by 1H NMR and found to range from 54 to 75%, resulting in calculated number average molecular weights of 38 200 to 46 000 Da. The glass transition temperature (Tg) of PVA (75 °C) was increased to substantially excel over that of polystyrene (PS, 100 °C), with polyvinyl aromatic acetal Tg values ranging from 114 to 157 °C. Heterogeneous degradation studies of polyvinyl vanillin acetal at room temperature indicated nearly complete hydrolysis over 24 hours in acidic aqueous media. For example, at pH = 1, the initial acetalization of 54% dropped to 0.8%, generating benign aromatic small molecules and water-soluble, biodegradable PVA.

Graphical abstract: Sustainable polyvinyl acetals from bioaromatic aldehydes

Supplementary files

Article information

Article type
Paper
Submitted
03 Feb 2017
Accepted
16 Mac 2017
First published
24 Mac 2017

Polym. Chem., 2017,8, 5049-5059

Sustainable polyvinyl acetals from bioaromatic aldehydes

M. Rostagno, S. Shen, I. Ghiviriga and S. A. Miller, Polym. Chem., 2017, 8, 5049 DOI: 10.1039/C7PY00205J

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