NDLI: A study of cyclic carbonate aminolysis at room temperature: effect of cyclic carbonate structures and solvents on polyhydroxyurethane synthesis

Content Provider	Royal Society of Chemistry (RSC)
Author	Auvergne, Rémi Blain, Marine Andrioletti, Bruno Boutevin, Bernard Cornille, Adrien Caillol, Sylvain
Copyright Year	2017
Abstract	In recent years, intensive research and development have been carried out for the synthesis of isocyanate free polyurethanes from the reaction between five-membered cyclic carbonates and amines to yield polyhydroxyurethanes (PHU). Nevertheless, this reaction presents two main drawbacks: the low reactivity of cyclic carbonate aminolysis and the low molar masses of synthesized PHUs. Firstly, our work intends to propose a wider reactivity study on various C5 and C6 in order to determine the influence of substituents attached to the cyclic carbonate and to compare the reactivity of C5 and C6 with exactly the same substituents. Moreover, we completed this study with new structures with promising reactivity such as C5 and C6 with ethyl-ester or trimethylhexanoate substituents that have never been studied in the literature. Hence, a range of cyclic carbonate models with different structures, 5-, 6-membered cyclic carbonate (C5, C6) or 5-membered-dithio-cyclic carbonate (Cs), were synthesized. Secondly, this kinetic study has brought to light a partial conversion of precursors during the aminolysis reaction that can be responsible for the low molar masses of PHUs. This partial conversion is caused mainly by the formation of hydrogen bonding inter- and intra-chains limiting the diffusivity of species during the polymerization. A model study showed that the use of protic solvents improves the reactivity of cyclic carbonates and increases the conversion during their aminolysis reaction. Therefore, this protic solvent gives its mobility back to the precursors by limiting the creation of hydrogen bonding inter- and intra-chains. Finally, the efficiency of protic solvents on the synthesis of PHU polymers was evaluated.
Starting Page	592
Ending Page	604
Page Count	13
File Format	HTM / HTML PDF
ISSN	17599954
Volume Number	8
Issue Number	3
Journal	Polymer Chemistry
DOI	10.1039/c6py01854h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Aminolysis Isocyanate Molar mass Polymerization Protic solvent
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Bioengineering Biomedical Engineering Polymers and Plastics

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