A Green Step to New Monomers and Their Polymerization

• Published in: ChemistrySelect (Weinheim) Vol. 5; no. 39; pp. 12109 - 12114
• Main Authors: Strehmel, Veronika, Strunk, David, Heinz, Markus, Walther, Sebastian
• Format: Journal Article
• Language: English
• Published: 22.10.2020
• Subjects: biomass; birch bark; green chemistry; polymerization; polymers
• ISSN: 2365-6549; 2365-6549
• DOI: 10.1002/slct.202002526

Extract obtained from the bark of Betula Pendula was treated with sodium hydroxide solution to obtain 4‐(4‐hydroxyphenyl)butan‐2‐one. New (meth)acrylates were synthesized on the basis of 4‐(4‐hydroxyphenyl)butan‐2‐one. Free radical polymerization of the new (meth)acrylates was compared with that of commercial monomers (e. g. phenyl(meth)acrylate, 2‐phenoxyethyl methacrylate, and benzyl methacrylate) in solution resulting in soluble polymers as expected in all examples. In contrast to this, free radical polymerization of 4‐(4‐acryloyloxyphenyl)butan‐2‐one in bulk resulted in a crosslinked material although an extremely high molecular weight soluble polymer was received in case of bulk polymerization of 4‐(4‐methacryloyloxyphenyl)butan‐2‐one. The 3‐oxobutyl substituent at the phenyl ring of these monomers may influence their radical polymerization. Furthermore, enzyme mediated radical polymerization and photoinitiated polymerization were applied for the polymer synthesis using 4‐(4‐methacryloyloxyphenyl)butan‐2‐one. Birch bark and a synthetic pathway were used for manufacturing of 4‐(hydroxyphenyl)butan‐2‐one. New (meth)acrylates were synthesized from 4‐(hydroxyphenyl)butan‐2‐one and polymerized using traditional free radical polymerization, enzyme mediated polymerization, and photoinitiated polymerization resulting in new polymers that were compared with polymers made from commercial monomers regarding yield, molecular weight, dispersity, and glass transition temperature. The 3‐oxobutyl substituent at the aromatic ring of the new monomers may influence their radical polymerization and the structure of the polymers obtained.