Biobased, Biodegradable, and Water-Soluble Amine-Functionalized Non-Isocyanate Polyurethanes for Potential Home Care Application

Non-isocyanatepolyurethanes (NIPUs) synthesized using bis-/poly(cycliccarbonate) and di-/polyamine monomers provide a safer alternativeto conventional polyurethanes (PUs) produced from highly toxic di-/polyisocyanatesand di-/polyols. Water-based NIPUs could potentially substitute waterbornePUs, particularly, in applications where the presence of minute amountsof isocyanate impurity in the final PU product might cause severeconsequences. Nevertheless, direct syntheses of water-soluble NIPUsare uncommon. Herein, we report a single-step synthesis of water-solubleand bio-derived linear amine-NIPUs by the polyaddition reaction ofsuccinic bis(cyclic carbonate) (SuBCC) with different commercial polyamines.These amine-NIPUs contain secondary (-NH-) or tertiary(-NR-) amine groups in their main chain imparting goodwater solubility/dispersibility. Consequently, the water-soluble amine-NIPUswere evaluated for their function as anti-soil/dirt redepositioningagents, one of the key ingredients present in laundry detergents usedin home care applications. It is demonstrated that amine-NIPUs inthis study are effective in retaining >90% whiteness (L*) of cotton and polyester cloths after model dirt deposition andwash cycle. Remarkably, these polymers were noncytotoxic when testedon human keratinocyte HaCaT cells and non-skin irritants by in vitro skin irritation assay using reconstructed humanepidermis, which emphasizes their suitability for home care applicationsfurther. The amine-NIPUs were also found to degrade slowly (65% in32 days) under hydrolytic conditions similar to that of seawater (pH8.4 at 23 & DEG;C) and were biodegradable in activated sludge (upto 66% in 28 days), as determined by Zahn Wellens OECD-302-B assay.This work may pave the way toward the development and utilizationof green, sustainable, and biodegradable NIPUs in home care and otherapplications, replacing the current toxic, nondegradable, and petroleum-basedingredients.

Automated summary

This study reports a single-step synthesis method for water-soluble and bio-derived linear amine-based non-isocyanatepolyurethanes (NIPUs). These polymers exhibit good water solubility and dispersion, making them potential candidates as anti-soil/dirt redepositioning agents in home care applications. They are also noncytotoxic and non-skin irritants, demonstrating their suitability for further use. The development and utilization of such green, sustainable, and biodegradable NIPUs may replace the current toxic and nondegradable ingredients in various applications.