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Sustainable polyvinyl acetals from bioaromatic aldehydes

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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

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Publication details

The article was received on 03 Feb 2017, accepted on 16 Mar 2017 and first published on 24 Mar 2017


Article type: Paper
DOI: 10.1039/C7PY00205J
Citation: Polym. Chem., 2017, Advance Article
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    Sustainable polyvinyl acetals from bioaromatic aldehydes

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

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