Room temperature synthesis of non-isocyanate polyurethanes (NIPUs) using highly reactive N-substituted 8-membered cyclic carbonates
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2016-02-16Autor
Yuen, Alexander
Bossion, Amaury
Gómez Bengoa, Enrique
Ruipérez Cillán, Fernando
Hedrick, James
Mecerreyes Molero, David
Yi, Yan Yang
Sardon Muguruza, Haritz
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Polymer Chemistry 7(11) : 2105-2111 (2016)
Resumen
There is a growing interest to develop green synthetic pathways towards industrially relevant polymers
such as polyurethanes without the use of toxic and dangerous isocyanate monomers. The most promising
route towards non-isocyanate polyurethanes (NIPUs) is the aminolysis of dicyclic carbonates derived
from renewable resources. Although, cyclic carbonates of 5- and 6-members have been successfully proposed,
aminolysis of these compounds requires the use of high temperatures to obtain high conversions
and subsequently high molecular weight NIPUs. Indeed, these cyclic carbonates do not allow the
achievement of high molecular weight NIPUs using low reactive diamines analogous to two of the most
industrially relevant aliphatic diisocyanates. Herein, we report a (bis) N-substituted 8-membered cyclic
carbonate that could be prepared from naturally abundant epoxides, diamines and dimethyl carbonate
using sustainable chemical routes. This N-substituted 8 membered cyclic carbonate appeared to be
much more reactive than the smaller 5- and 6-membered cyclic carbonates. Due to this increased
reactivity, we obtained high molecular weight NIPUs using a variety of diamines, including industrially
relevant hindered aliphatic diamines, such as 5-amino-1,3,3-trimethylcyclohexanemethylamine (IPDA)
and 4,4’-methylenebis(cyclohexylamine). The synthesis of NIPUs was demonstrated at room
temperature without the need for any additional catalyst. Altogether, this paper shows that (bis) N-substituted
8-membered cyclic carbonates are ideal starting materials for the synthesis of sustainable non-isocyanate
polyurethanes (NIPUs).