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      Microwave-Assisted Syntheses in Recyclable Ionic Liquids: Photoresists Based on Renewable Resources

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          Abstract

          The copoly(2-oxazoline) pNonOx 80- stat-pDc =Ox 20 can be synthesized from the cationic ring-opening copolymerization of 2-nonyl-2-oxazoline NonOx and 2-dec-9′-enyl-2-oxazoline Dc =Ox in the ionic liquid n-hexyl methylimidazolium tetrafluoroborate under microwave irradiation in 250 g/batch quantities. The polymer precipitates upon cooling, enabling easy recovery of the polymer and the ionic liquid. Both monomers can be obtained from fatty acids from renewable resources. pNonOx 80- stat-pDc =Ox 20 can be used as polymer in a photoresist (resolution of 1 μm) based on UV-induced thiol–ene reactions.

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          Most cited references43

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          New frontiers in materials science opened by ionic liquids.

          Ionic liquids (ILs) including ambient-temperature molten salts, which exist in the liquid state even at room temperature, have a long research history. However, their applications were once limited because ILs were considered as highly moisture-sensitive solvents that should be handled in a glove box. After the first synthesis of moisture-stable ILs in 1992, their unique physicochemical properties became known in all scientific fields. ILs are composed solely of ions and exhibit several specific liquid-like properties, e.g., some ILs enable dissolution of insoluble bio-related materials and the use as tailor-made lubricants in industrial applications under extreme physicochemical conditions. Hybridization of ILs and other materials provides quasi-solid materials, which can be used to fabricate highly functional devices. ILs are also used as reaction media for electrochemical and chemical synthesis of nanomaterials. In addition, the negligible vapor pressure of ILs allows the fabrication of electrochemical devices that are operated under ambient conditions, and many liquid-vacuum technologies, such as X-ray photoelectron spectroscopy (XPS) analysis of liquids, electron microscopy of liquids, and sputtering and physical vapor deposition onto liquids. In this article, we review recent studies on ILs that are employed as functional advanced materials, advanced mediums for materials production, and components for preparing highly functional materials.
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            Toxicity of ionic liquids: eco(cyto)activity as complicated, but unavoidable parameter for task-specific optimization.

            Rapid progress in the field of ionic liquids in recent decades led to the development of many outstanding energy-conversion processes, catalytic systems, synthetic procedures, and important practical applications. Task-specific optimization emerged as a sharpening stone for the fine-tuning of structure of ionic liquids, which resulted in unprecedented efficiency at the molecular level. Ionic-liquid systems showed promising opportunities in the development of green and sustainable technologies; however, the chemical nature of ionic liquids is not intrinsically green. Many ionic liquids were found to be toxic or even highly toxic towards cells and living organisms. In this Review, we show that biological activity and cytotoxicity of ionic liquids dramatically depend on the nature of a biological system. An ionic liquid may be not toxic for particular cells or organisms, but may demonstrate high toxicity towards another target present in the environment. Thus, a careful selection of biological activity data is a must for the correct assessment of chemical technologies involving ionic liquids. In addition to the direct biological activity (immediate response), several indirect effects and aftereffects are of primary importance. The following principal factors were revealed to modulate toxicity of ionic liquids: i) length of an alkyl chain in the cation; ii) degree of functionalization in the side chain of the cation; iii) anion nature; iv) cation nature; and v) mutual influence of anion and cation.
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              Undecylenic acid: a valuable and physiologically active renewable building block from castor oil.

              A lot of attention is currently being paid to the transition to a biobased economy. In this movement, most efforts concentrate on the development of bioenergy applications including bioethanol, biodiesel, thermochemical conversion of biomass, and others. However, in the energy sector other nonbiomass alternatives are known, whereas no valuable alternatives are available when thinking about chemical building blocks. Therefore, it is also essential to develop new routes for the synthesis of bio-based chemicals and materials derived thereof. Such intermediates can originate either from plants or from animals. Castor oil is a non-edible oil extracted from the seeds of the castor bean plant Ricinus communis (Euphorbiaceae), which grows in tropical and subtropical areas. Globally, around one million tons of castor seeds are produced every year, the leading producing areas being India, PR China, and Brazil.2 10-Undecenoic acid or undecylenic acid is a fatty acid derived from castor oil that, owing to its bifunctional nature, has many possibilities to develop sustainable applications.
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                Author and article information

                Journal
                ChemSusChem
                ChemSusChem
                cssc
                Chemsuschem
                Blackwell Publishing Ltd (Oxford, UK )
                1864-5631
                1864-564X
                October 2015
                10 September 2015
                : 8
                : 20
                : 3401-3404
                Affiliations
                [[a] ]IPREM, UMR 5254 UPPA/CNRS, Hélioparc 2 Avenue du Président Angot, 64053, Pau CEDEX 09 (France) E-mail : stephanie.reynaud@ 123456univ-pau.fr
                [[b] ]Polymer Competence Center Leoben (PCCL) Roseggerstrasse 12, 8700, Leoben (Austria)
                [[c] ]Institute for Chemistry and Technology of Materials, Graz University of Technology, NAWI Graz Stremayrgasse 9, 8010, Graz (Austria)
                [[d] ]Chair of Chemistry of Polymeric Materials, University of Leoben Otto-Gloeckel-Strasse 2, 8700, Leoben (Austria)
                [[e] ]Anton Paar GmbH (Ltd.) Anton-Paar-Strasse 20, 8054, Graz (Austria)
                Author notes
                [[+]]

                These authors contributed equally to this work.

                Supporting Information and ORCIDs from the authors of this article are available on the WWW under http://dx.doi.org/10.1002/cssc.201500847.

                Article
                10.1002/cssc.201500847
                4641455
                26354027
                a83bcf8d-ce91-40fe-b3a0-ab8a955eab6b
                © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

                This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

                History
                : 22 June 2015
                Categories
                Communications

                Sustainable & Green chemistry
                copolymerization,ionic liquids,microwave chemistry,renewable resources,ring-opening polymerization

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