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Polymer Chemistry Vol - 5 Issue - 8

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Cyclic and spirocyclic polyacetal ethers from lignin-based aromatics

Content Provider	Royal Society of Chemistry (RSC)
Author	Rostagno, Mayra Pemba, Alexander G. Miller, Stephen A. Lee, Tanner A.
Copyright Year	2014
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.
Starting Page	3214
Ending Page	3221
Page Count	8
File Format	HTM / HTML PDF
ISSN	17599954
Volume Number	5
Issue Number	9
Journal	Polymer Chemistry
DOI	10.1039/c4py00178h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Lignin PTOL Thermogravimetric analysis Pentaerythritol Polyoxymethylene Glass transition Hydrochloric acid Hydrolysis Ethylvanillin Dynamic light scattering Polymer degradation Dimethyl sulfoxide Syringaldehyde Vanillin Spiro compound 4-Hydroxybenzaldehyde
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Bioengineering Biomedical Engineering Polymers and Plastics

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