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In many reports, cellulose and nanocellulose have been carbamated using 2,4-toluene diisocyanate (2,4-TDI) to allow the grafting of molecules or polymers onto their surfaces. Such a process usually involves the reaction of the more reactive isocyanate group of TDI (para-NCO) selectively with a hydroxyl group from the cellulose surface, followed by the reaction of the free isocyanate (ortho-NCO) with a desired molecule. After the first step, it is not possible, using elemental analysis, to determine the amount of ortho-NCO on the cellulosic surface, as an ideal para/ortho selectivity is difficult to obtain. This paper presents a simple method for the quantification of ortho-NCOs on the surface of cellulose nanocrystals upon TDI-based carbamation. It relies on the pH increase upon a complete hydrolysis of ortho-NCOs to amine groups using acidified dimethylsulfoxide. The method was found to be accurate and valid for a degree of substitution of up to 20%.

A Simple Method for the Quantification of Free Isocyanates on the Surface of Cellulose Nanocrystals upon Carbamation using Toluene Diisocyanate