Jump to main content
Jump to site search

Issue 9, 2014
Previous Article Next Article

Cyclic and spirocyclic polyacetal ethers from lignin-based aromatics

Author affiliations

Abstract

Monomers structurally resembling lignin were prepared by reacting 4-hydroxybenzaldehyde, vanillin, syringaldehyde, (each bio-available) or ethylvanillin (synthetic) with dibromoethane, yielding dialdehydes CHO–Ar–OCH2CH2O–Ar–CHO. Condensation copolymerization with tetraols catalyzed by para-toluene sulfonic acid yielded polyacetal ethers with cyclic acetals in the case of di-trimethylolpropane (di-TMP) and spirocyclic acetals in the case of pentaerythritol (PTOL). Number average molecular weights (Mn) were in the range of 10 600 to 22 200, although the insolubility of those polymers based on 4-hydroxybenzaldehyde precluded this measurement. The polymers are thermally robust and exhibit 5% mass loss via thermogravimetric analysis in the range of 307–349 °C. Those copolymers based on PTOL displayed glass transition (Tg) temperatures (108–152 °C) at least 40 °C higher than their di-TMP analogues (68–98 °C), highlighting the added rigidity conferred by spirocyclic acetals versus cyclic acetals. Preliminary degradation studies were conducted in dimethyl sulfoxide with 0.5% added aqueous HCl (concentrated or 2 M). Dynamic light scattering confirmed the facile hydrolysis of the polymers. Generally, polymer degradation was faster with a higher acid concentration and copolymers from the PTOL tetraol were more resistant to hydrolysis than those from the di-TMP tetraol.

Graphical abstract: Cyclic and spirocyclic polyacetal ethers from lignin-based aromatics

Back to tab navigation

Supplementary files

Article information


Submitted
07 Feb 2014
Accepted
21 Feb 2014
First published
25 Feb 2014

Polym. Chem., 2014,5, 3214-3221
Article type
Paper

Cyclic and spirocyclic polyacetal ethers from lignin-based aromatics

A. G. Pemba, M. Rostagno, T. A. Lee and S. A. Miller, Polym. Chem., 2014, 5, 3214
DOI: 10.1039/C4PY00178H

Social activity

Search articles by author

Spotlight

Advertisements