Degradability, thermal stability, and high thermal properties in spiro polycycloacetals partially derived from lignin. Issue 41 (5th October 2021)

• Record Type: Journal Article
• Authors: Shen, Minjie; Vijjamarri, Srikanth; Cao, Hongda; Solis, Karla; Robertson, Megan L.
• Is Part Of: Polymer chemistry. Volume 12:Issue 41(2021)
• Page Start: 5986
• Page End: 5998
• Publication Date: 2021-10-05
• Subjects: Polymers -- Periodicals; Macromolecules -- Periodicals; Polymerization -- Periodicals; 547.705
• DOI: 10.1039/d1py01017d
• Languages: English
• ISSNs: 1759-9954

Abstract

Abstract : Spiro polycycloacetals were synthesized from vanillin and syringaldehyde, along with high-performance co-monomers, exhibiting high glass transition temperatures and thermal stabilities, and rapid rates of hydrolysis in acidic solutions. Abstract : A series of partially bio-based spiro polycycloacetals was synthesized using lignin-based feedstocks, vanillin and its derivative syringaldehyde, along with pentaerythritol and commercially available co-monomers including 4, 4′-difluorobenzophenone (DFP) and bis(4-fluorophenyl) sulfone (DFS). These spiro polycycloacetals displayed high thermal stabilities (degradation temperatures in the range of 343–370 °C, as quantified by 5% mass loss) and high glass transition temperatures (in the range of 179–243 °C). While DFS-containing polymers were amorphous, DFP-containing polymers were semi-crystalline with high melting temperatures (in the range of 244–262 °C). The hydrolytic degradation behavior of one spiro polycycloacetal, derived from vanillin and DFP, was investigated. Importantly, the spiro polycycloacetal was rapidly degraded to small molecules and oligomeric byproducts under acid-catalyzed conditions. This class of spiro polycycloacetals is therefore an important contributor to the development of more easily degradable polymers which also retain sufficiently high thermal properties and thermal stability.