An important step towards strong and durable biobased plastics
Overcoming the low reactivity of biobased secondary diols in polyester synthesis
Peer-Reviewed PublicationIMAGE: TENSILE TESTING OF THE DEVELOPED BIO-BASED POLYMER (LEFT) AND A SAMPLE OF POLYMER FILM (RIGHT) view more
CREDIT: UVA, HIMS
In a recent paper in Nature Communications, researchers at the Industrial Sustainable Chemistry group led by Prof. Gert-Jan Gruter take an important step towards the production of fully biobased, rigid polyesters. They present a simple, yet innovative, synthesis strategy to overcome the inherently low reactivity of biobased secondary diols and arrive at polyesters that have very good mechanical- and thermal properties, and at the same time high molecular weights. It enables the production of very strong and durable biobased plastics from building blocks that are already commercially available.
The research described in the Nature Communications paper was carried out within the RIBIPOL project funded by the Dutch Research Council NWO with contributions from industry, notably LEGO and Avantium. The toy company supported the project as part of the search for non-fossil alternatives for its plastic bricks. Avantium is interested in bottle- and film applications. First author of the paper is PhD student Daniel Weinland, who graduated on 27 October. In total, 5 PhD students are involved in the RIBIPOL project, of which 2 have defended their thesis recently.
In general, polyester plastics are synthesized from small dialcohol and diacid molecules. These monomers are coupled in a condensation reaction, resulting in a long polymer chain of molecular building blocks in an alternating fashion. The macroscopic material properties result both from the number of building blocks that make up the polymer chain, and from the inherent properties of the monomers. In particular their rigidity is key to a firm, strong and durable plastic. In this regard, the glucose-derived dialcohol isosorbide is unique among potential biobased monomers. It has a very rigid molecular structure and is already industrially available.
However, isosorbide is rather unreactive, and in the past two decades it has proven quite challenging to obtain useful isosorbide-based polyesters. It was nearly impossible to arrive at sufficiently long polymer chains (to achieve a certain ductility) while incorporating sufficiently high amounts of isosorbide (to arrive at a strong and durable material).
Incorporating an aryl alcohol
Weinland and his RIBIPOL colleagues have overcome this impasse by incorporating an aryl alcohol in the polymerization process. This leads to in situ formation of reactive aryl esters and a significant enhancement of the end group reactivity during polycondensation, the last stage of polyester synthesis when isosorbides low reactivity inhibits chain growth in traditional melt polyesterification. As a result, high molecular weight materials could be produced with incorporation of high fractions of the biobased, rigid secondary diol, even up to 100 mol%. For the first time high molecular weight poly(isosorbide succinate) could be produced, the polyester obtained from isosorbide and succinic acid. The resulting strong plastics outperform existing plastics like PET in terms of heat resistance, which is for instance relevant for re-use - think of washing bottles that takes place at 85 °C. The isosorbide-based polymers also show promising barrier and mechanical properties that can outperform common fossil-based materials.
The novel polymerisation approach described in the paper is characterized by operational simplicity and the use of standard polyester synthesis equipment. It suits both existing and novel polyester compositions; the researchers foresee exploration of previously inaccessible polyester compositions based on monomers with a low reactivity but also the application of similar methods in other classes of polymers such as polyamides and polycarbonates.
Synthesis of high molecular weight poly(isosorbide succinate) with an aryl alcohol. a: Monomer synthesis from glucose, obtainable from either first or second generation biomass. b: Synthesis of poly(isosorbide succinate) from succinic acid, isosorbide and p-cresol. c: Poly(isosorbide succinate) molecular weights obtained with a reactive solvent (p-cresol), no solvent and an unreactive solvent (1,4-dimethoxybenzene) under comparable reaction conditions
JOURNAL
Nature Communications
METHOD OF RESEARCH
Experimental study
SUBJECT OF RESEARCH
Not applicable
ARTICLE TITLE
Overcoming the low reactivity of biobased, secondary diols in polyester synthesis
Biopolymers Towards Green and Sustainable Development
Recently natural biodegradable excipients gained significant attention due to their sustainability and engineered applications. Innovative technologies to transform these materials into value-added chemicals via novel graft-polymerization or co-processing techniques for the production of high-performance multifunctional and low-cost polymers with tunable structures are key parts of its sustainable development.
In the book “Biopolymers Towards Green and Sustainable Development“ we have elaborated various important issues that relates with topic such as overview of bio-based polymers, impact of non-biodegradable polymers on the environment and health, emerging new sources of biodegradable polymers, structural and morphological characterization techniques, thermomechanical properties, biodegradable plastics from biopolymers, pharmaceutical, biomedical, and textile applications, and pharmacokinetics and pharmacodynamics with a brief on bibliometric meta-analysis on bio-based pharmaceutical excipients. The chapters are beneficial for the graduate and researcher who are working in the similar field. Moreover, the bibliometric analysis provides an update to researcher about potential scientist involve in the exploitation of polymeric research. In addition, meta-analysis provides details on active country, organization, and funding agencies embroil in research based on development and assessment of multifarious biodegradable polymers.
The key features of books “Biopolymers Towards Green and Sustainable Development” are as up-dated summary on recently discovered natural polymeric materials, a thorough breakdown of the vast range of application areas including fabrication of conventional and novel drug delivery, polymeric scaffolds, composites, microneedles, and green synthesis of metallic nanoparticles, summary of pharmacology and pharmacokinetics on the inactive pharmaceutical ingredient, and bibliometric meta-analysis indicating potential collaboration between country, organization, institution, and authors with a view on recent ongoing trends with biopolymers.
About the editor:
Dr. Sudarshan Singh presently working as a University Reinventing Postdoctoral research scholar at Chiang Mai University, Thailand. He has authored several technical books and books chapters for pharmacy graduate students of Savitribai Phule Pune University, India. He has published more than hundreds of research papers in reputed peer-reviewed journals. He has presented many papers and participated as a resource person in International and National conferences. He is ratified and approved by Pacific University, Rajasthan, India as a Ph.D. guide. He has registered three patents on his credit. He is an editorial member of Science Domain International (India, UK, and the USA). He is a reviewer of various international journals. He has ten years of teaching experience in undergraduate and postgraduate courses of pharmacy with more than five years of research experience. He has guided several undergraduate and postgraduate students in their project work. Moreover, during his postdoctoral research at Prince of Songkhla University and Walailak University, Thailand, he co-supervised doctorate students. He is a life member of professional bodies such as the Society of Pharmacovigilance India and a registered pharmacist at the State Pharmacy Council of Chhattisgarh, India. He has received several grants from the government of Gujarat and Savitribai Phule Pune University Maharashtra, India. He has received travel grants from the Indian Council of Medical Research, Delhi, India, and the Centre for International Co-operation in Science, Tamil Nadu, India.
Dr. Warangkana Chunglok presently working as Associate Professor at the School of Allied Health Sciences, Walailak University, Thailand. She received Royal Golden Jubilee Scholarship from Thailand Research Fund, Thailand, and Deutscher Academischer Austausch Dienst (DAAD), Germany for perusing her Ph.D. Furthermore, she has received several awards from Walailak University, Thailand. She has sixteen years of teaching and research experience. She is one of the expert scientists in molecular biology of cancer, natural product-based drug discovery for cancers and inflammatory-related diseases, and therapeutic agents from medicinal plants for muscle wasting following stroke. Her research works are conducted both in national collaboration with other universities in Thailand and international collaboration with European Union research institutes. Her background experience includes experiments in molecular biology, in vitro and in vivo study, natural products drug discovery, evaluation of natural compounds and their synthetic analogues from medicinal plants as potential drug leads for the treatment of various types of cancers, inflammatory diseases, and stroke.
Keywords:
Biopolymer, Thermoplastic, Bio-based polymer, Fibers, Biodegradable polymers, Cellulose, Natural polymer, Polymer pharmacokinetics, Polymer structural characterization, Plant mucilage, Polymer thermomechanical characterization, Bibliometric analysis, Additive manufacturing, Drug delivery, Electrospinning, Modified drug delivery, Marine polymers, Novel drug delivery, Bioplastic, Sustained or controlled release drug delivery.
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