Citation: Gawdzik, B.;
Bukowska-
´
Sluz, I.; Koziol, A.E.;
Mazur, L. Synthesis and
Characterization of Biodegradable
Polymers Based on Glucose
Derivatives. Materials 2023, 16, 253.
https://doi.org/10.3390/
ma16010253
Academic Editor: Halina Kaczmarek
Received: 6 December 2022
Revised: 21 December 2022
Accepted: 24 December 2022
Published: 27 December 2022
Copyright: © 2022 by the authors.
Licensee MDPI, Basel, Switzerland.
This article is an open access article
distributed under the terms and
conditions of the Creative Commons
Attribution (CC BY) license (https://
creativecommons.org/licenses/by/
4.0/).
materials
Article
Synthesis and Characterization of Biodegradable Polymers
Based on Glucose Derivatives
Barbara Gawdzik * , Izabela Bukowska-
´
Sluz, Anna E. Koziol and Liliana Mazur
Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie-Sklodowska University, Gliniana 33,
20-614 Lublin, Poland
* Correspondence: barbara.gawdzik@mail.umcs.pl
Abstract: Syntheses of two new monomers, namely the glucose derivatives 2,3,4,6-tetra-O-acetyl-1
methacryloyl-glucopyranose (MGlc) and 2,3,4,6 tetra-O-acetyl-1-acryloylglucopyranose (AGlc), are
presented. Their chemical structures were determined by the FTIR,
1
H and
13
C NMR spectroscopies,
the single-crystal X-ray analysis, supported by the powder X-ray diffraction, and the DSC anal-
yses. Molecules of both monomers exist in the β-anomeric form in the solid state. The variable
temperature X-ray diffraction studies, supported by the DSC analyses, revealed AGlc’s propensity
for polymorphism and temperature-induced phase transitions. MGlc and AGlc crystallised from
methanol were polymerized or copolymerized with methyl methacrylate and N-vinylpyrrolidone.
The biodegradabilities of polymers as well as thermal and optical properties were studied. The results
show that some properties of the obtained homopolymers and copolymers resemble those of PMMA.
The main difference is that the AGlc and MGlc homopolymers are biodegradable while PMMA is
not. The ternary copolymers, i.e., MGlc/AGlc-MMA-NVP lose more than 10% of their weight after
six months.
Keywords: glucose; acryl- and methacryl derivatives; copolymerization; biodegradable polymer;
polymorphism of monomer
1. Introduction
Carbohydrates are the most abundant class of organic compounds found in living
organisms. They are synthesised by green plants during the complex process of photosyn-
thesis, in which sunlight provides the energy to transform carbon dioxide and water into
glucose. Then, many glucose molecules are combined by covalent bonds, creating a reserve
material in the form of plant cellulose or starch [1,2].
At present, sugars and their processed products are used in different areas of industry.
Lately, they have been increasingly used for the production of plastic packaging [3]. Most
plastic packaging is manufactured from synthetic polymers which are very durable and
hardly decompose in the environment. This contributes to the increasing amount of plastic
waste, causing serious environmental and economic problems. Therefore, the ideal solution
to this problem is to produce plastics with biodegradable components [4–8].
Two approaches are usually used, involving the creation of blends with biodegrad-
able fillers, for example, with starch, or research on the synthesis of polymers from new
monomers obtained as a result of chemical modification of natural compounds [9,10].
Sugars are an attractive substrate for the synthesis of new polymers due to their
abundance and availability. Incorporating them into complex chemical structures increases
the likelihood of their disintegration.
However, polysaccharides are used for this purpose much more often than simple
sugars. Among simple sugar-derived monomers, those containing bicyclic diols based on
1,4:3,6-dianhydrohexitols or diols derived from D-glucitol are studied extensively [11–15].
Materials 2023, 16, 253. https://doi.org/10.3390/ma16010253 https://www.mdpi.com/journal/materials