화학공학소재연구정보센터
Journal of Applied Polymer Science, Vol.74, No.11, 2764-2772, 1999
Preparation of cellulose derivatives containing carbazole chromophore
Cellulose derivatives containing long hydrocarbon side chains and the carbazole chromophore are prepared. N-4'-Bromobutylcarbazole is first synthesized from carbazole and 1,4-dibromobutane. Alkylated carbazole is then reacted with cellulose acetate in dimethyl sulfoxide solution to produce cellulose ethers containing the desired chromophore. Polymers containing a mixture of alkyl side chains are also prepared by the subsequent addition of 1-bromododecane to the reaction mixture. Characterization of the resulting cellulose derivatives by FTIR spectroscopy indicates that the deacetylation of cellulose acetate and the subsequent etherification are both complete. In addition, the incorporation of the carbazole chromophore is clearly shown by H-1- and C-13-NMR spectroscopy. Polymers of different carbazole content, ranging from 2.9 to 1.1 chromophores per anhydroglucose repeat unit, are obtained by varying the reaction conditions. Substitution is found to be controlled primarily by the quantity of alkylating agent introduced while variation of the reaction time has little effect. This method is used to prepare (dodecyl)(y)(N-4'-carbazolylbutyl)(x)cellulose, (decyl)(y)(N-4'-carbazolylbutyl)(x)cellulose, and (butyl)(y)(N-4'-carbazolylbutyl)(x)cellulose. Cellulose acetate can be replaced by (methyl)cellulose as the starting material to obtain analogous products.