Revisiting the Synthesis of Cellulose Acrylate and Its Modification via Michael Addition Reactions
Hiroya Okamoto, Tsuyoshi Taniguchi, Motohiro Takekuma, Asami S. Mashio, Kuo Hong Wong, Hiroshi Hasegawa, Tatsuya Nishimura, Katsuhiro Maeda
Abstract
The synthesis of cellulose acrylate from cellulose with acryloyl chloride has been problematic due to unexpected gelation of the reaction mixture, but we discovered that the use of bulky amines was crucial for the reproducibility of the synthesis of cellulose acrylate. The solubility of the obtained cellulose acrylate depended on the reaction conditions due to the possible cross-linking oxa-Michael reaction between a remaining hydroxy group and the introduced acrylate group. The synthesized cellulose acrylate worked as a useful precursor of chemically modified cellulose materials because it reacted with various functionalized nucleophiles such as secondary amines and thiols as a Michael donor. This method was applied to the synthesis of N -methyl- d -glucamine-modified cellulose that works as an adsorbent for the removal of B(OH) 3 in water.