Choong, P. S., Tam, K. W. E., Chong, N. X., Seayad, A. M., Seayad, J., & Jana, S. (2023). Biobased, Biodegradable, and Water-Soluble Amine-Functionalized Non-Isocyanate Polyurethanes for Potential Home Care Application. ACS Applied Polymer Materials, 5(7), 5503–5513. https://doi.org/10.1021/acsapm.3c00827
Abstract:
Non-isocyanate polyurethanes (NIPUs) synthesized using bis-/poly(cyclic
carbonate) and di-/polyamine monomers provide a safer alternative to conventional polyurethanes
(PUs) produced from highly toxic di/polyisocyanates and di/polyols. Water based NIPUs could
potentially substitute waterborne PUs, particularly, in applications where the presence of minute
amounts of isocyanate impurity in the final PU product might cause severe consequences.
Nevertheless, direct syntheses of water-soluble NIPUs are uncommon. Herein we report a single
step synthesis of water-soluble and bio-derived linear amine-NIPUs by the polyaddition reaction
of succinic bis(cyclic carbonate) (SuBCC) with different commercial polyamines. These amineNIPUs contain secondary (-NH-) or tertiary (-NR-) amine groups in their main-chain imparting
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good water solubility/dispersibility. Consequently, the water-soluble amine-NIPUs were evaluated
for their function as anti-soil/dirt redepositioning agents, one of the key ingredients present in
laundry detergents used in home care applications. It is demonstrated that amine-NIPUs in this
study are effective in retaining >90% whiteness (L*) of cotton and polyester cloths after model
dirt deposition and wash cycle. Remarkably, these polymers were non-cytotoxic when tested on
human keratinocyte HaCaT cells and non-skin irritant by in vitro skin irritation assay using
reconstructed human epidermis, which emphasizes their suitability for home care application
further. The amine-NIPUs were also found to degrade slowly (65% in 32 days) under hydrolytic
conditions similar to that of sea water (pH 8.4 at 23oC), and were biodegradable in activated sludge
(up to 66% in 28 days) as determined by Zahn Wellens OECD-302-B assay. This work may pave
the way toward the development and utilization of green, sustainable and biodegradable NIPUs in
home care and other applications replacing current toxic, nondegradable, and petroleum-based
ingredients.
License type:
Publisher Copyright
Funding Info:
This research / project is supported by the Agency for Science, Technology and Research (A*STAR) - Advanced Manufacturing and Engineering (AME) IAF-PP Specialty Chemicals Programme
Grant Reference no. : A1786a0027