Cellulose derivatives with adamantoyl groups

Abstract

AbstractA new synthesis pattern of adamantoyl esters of cellulose (AdTMSC) is described. The process was approached by two steps. The first one consists in the obtaining of trimethylsilylcellulose (TMSC), by reacting cellulose in N,N‐dimethylacetamide/lithium chloride (DMA/LiCl) solution with chlorotrimethylsilane and hexamethyldisilazane. The AdTMSC was synthesized by reacting trimethylsilylcellulose with 1‐adamantanecarbonyl chloride, at 130°C. The obtained compounds were characterized by elemental analysis, 1H and 13C NMR, FTIR spectroscopy, thermogravimetry method, and X‐ray diffraction. From 1H NMR spectroscopy and elemental analyses, the degree of substitution (DS) of the cellulose derivatives was established. The AdTMSC is soluble in common organic solvent like chloroform, THF, and DMSO. As revealed by 13C NMR spectroscopy, a faster reaction takes place at the O (6)H group from AGU compared with O (2)H or O(3)H groups. Furthermore, other important properties were established by X‐ray diffraction and thermogravimetry method. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 100: 105–112, 2006