화학공학소재연구정보센터
Reactive & Functional Polymers, Vol.42, No.1, 103-109, 1999
Ionic cellulose derivatives: synthesis of sodium 6-deoxycellulose-6-sulfonate with high degree of substitution
The Strecker synthesis of sodium 6-deoxycellulose-6-sulfonate (Cell-sulfo) was carried out using 6-bromo-6-deoxycellulose (degree of bromine substitution, about 0.9) in saturated aqueous solutions of sodium sulfite, sodium hydrogen sulfite and their mixture under reflux and at 70 degrees C. The structure of Cell-sulfo was confirmed with H-1 and C-13 NMR spectroscopic analyses. Samples obtained were soluble in water over a wide pH range and the highest degree of sulfonate substitution exceeded 0.8 under optimum conditions; 6-bromo-6-deoxyglucose repeating units of Cell-Br were converted selectively to 6-deoxyglucose-6-sulfonate repeating units of Cell-sulfo with the conversion higher than 90% under neutral conditions in the mixture solution. In the saturated sodium sulfite solution, the reaction was fast but sulfonate groups formed were partly lost at longer reaction periods. Under reflux conditions in the saturated sodium hydrogen sulfite solution, the reaction rate was close to that observed for the reaction in the mixture solution. However, the reaction was slow at 70 degrees C and the conversion to the Cell-sulfo repeating units was around 10%.