1. Phosphate functionalized nonisocyanate polyurethanes with bio-origin, water solubility and biodegradability.
- Author
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Tam, Eric Kwok Wai, Chong, Ning Xi, Choong, Ping Sen, Sana, Barindra, Seayad, Abdul Majeed, Jana, Satyasankar, and Seayad, Jayasree
- Subjects
POLYMERS ,LINEAR polymers ,MOLECULAR weights ,SUSTAINABLE chemistry ,SOLUBILITY ,COORDINATION polymers ,PHOSPHATES ,PHOSGENE ,POLYURETHANES - Abstract
Nonisocyanate polyurethanes (NIPUs) are an emerging class of polyurethanes produced by circumventing the use of hazardous isocyanates and phosgene in their synthetic routes. In this study, we introduce a novel class of water-soluble/dispersible nonisocyanate polyurethanes (NIPUs) containing phosphate pendant groups, referred to as NIPU phosphate monoesters, by applying green chemistry principles. Linear NIPU polymers with number average molecular weight (M
n ) values ranging between 7400 and 13 600 Da and weight average molecular weight (Mw ) values between 13 900 and 27 800 Da were synthesised by the polymerization of bio-derived cyclic biscarbonates 4,4′-(((furan-2,5-diylbis(methylene)) bis(oxy))bis(methylene)) bis(1,3-dioxolan-2-one) (FuBCC) and bis((2-oxo-1,3-dioxolan-4-yl)methyl) succinate (SuBCC) with 1,5-pentanediamine (cadaverine) by utilizing green solvents. Subsequent functionalization of the resultant NIPUs via mild and selective phosphorylation using tetrabutylammonium dihydrogenphosphate (TBAP) as a phosphate source delivered NIPU phosphate monoesters containing up to 50% phosphate functionality as determined by1 H NMR. Interestingly, these phosphate-containing NIPUs were soluble/dispersible in water without the need for any external surfactants/co-solvents and demonstrated inherent aerobic biodegradability (56–75% in 28 days). Furthermore, the NIPU phosphate monoesters exhibited remarkable biocompatibility, showing slight to no growth inhibition of human keratinocyte HaCaT cells at concentrations up to 1 mg mL−1 . In vitro skin irritation assays on reconstructed human epidermis confirmed their non-skin irritant properties. These NIPU phosphate monoesters also exhibited multifunctional characteristics including oil-in-water emulsion stabilization ability and antimicrobial activity. This work emphasizes the scope and potential of these bio-derived, non-toxic and biodegradable nonisocyanate polyurethane phosphate monoesters as multifunctional additives in personal care/cosmetic applications. [ABSTRACT FROM AUTHOR]- Published
- 2024
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