CHEN Yu, YANG Kai, YE Yanchun, WANG Liye, CHU Liqiu, TAN Huimin. PREPARATION OF CHITOSAN IMMOBILIZED WITH β-CD AT C6 POSITION BY A NUCLEOPHILIC DISPLACEMENT REACTION[J]. Acta Polymerica Sinica, 2009,(7):712-716.
CHEN Yu, YANG Kai, YE Yanchun, WANG Liye, CHU Liqiu, TAN Huimin. PREPARATION OF CHITOSAN IMMOBILIZED WITH β-CD AT C6 POSITION BY A NUCLEOPHILIC DISPLACEMENT REACTION[J]. Acta Polymerica Sinica, 2009,(7):712-716. DOI: 10.3724/SP.J.1105.2009.00712.
A novel reaction route to prepare the derivate of chitosan with β-CD immob ilized at C6 position is proposed. It is reliable and of high efficiency.The a mi no group of the chitosan was protected by reacting with the benzaldehyde
and th e schiff base stucture was generated.The hydroxyl group in the schiff base chito san was tosylated by reacting with p-toluenesulfonyl chloride.Then the mono amino substituted β-cyclodextrin was immobilized onto C6 position of ch itosan by a nucleophilic displacement reaction between the tosylated chitosan an d the amino in cyclodextrin derivate.Finally
the schiff base structure was depro tected in the acetic acid solution
and β-CD immobilization derivate of ch itosan on C6-OH (CTS-CD) was prepared.The chemical structure of each resulta nts was analyzed by FTIR
13C-NMR
elemental analysis and UV
respecti vely.The UV absorption peak around 490 nm could be observed for the concentr ated sulfuric acid hydrolysis products of CTS-CD.However
the corresponding hydrolysi s products of CTS did not show any absorption peak near this range.By drawing th e calibration curve of the concentrated sulfuric acid hydrolysis products of β-CD through the UV spectrum
the immobilization amount of β-CD on the C6 position of chitosan could be quantitative detected.The obtained immobiliza ti on amount was 170.81 μmol.g-1
which was by head and shoulders high tha n the c orresponding values reported in literature.The crystallization properties of each resultants were studied through XRD characterization.