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 Ақп. 2017
Accepted
16 Нау. 2017
First published
24 Нау. 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements