Homogeneous synthesis and characterization of chitosan ethers prepared in aqueous alkali/urea solutions

被引:62
作者
Cao, Jinfeng
You, Jun
Zhang, Lina
Zhou, Jinping [1 ]
机构
[1] Wuhan Univ, Minist Educ, Dept Chem, Wuhan 430072, Hubei, Peoples R China
基金
中国国家自然科学基金; 国家高技术研究发展计划(863计划);
关键词
Chitosan ethers; Aqueous alkali/urea solution; Homogeneous synthesis; Reactivity; Degree of substitution; CARBOXYMETHYL CHITOSAN; METHYLATED CHITOSAN; BIOMEDICAL APPLICATIONS; HYDROXYPROPYL CHITOSAN; ANTIBACTERIAL ACTIVITY; HYDROGELS; DERIVATIVES; CELLULOSE; CHITIN; QUATERNIZATION;
D O I
10.1016/j.carbpol.2018.01.010
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The etherification of chitosan dissolved in aqueous LiOH/KOH/urea solutions was conducted for the first time. The structure and solution properties of the chitosan ethers were characterized using FT-IR, NMR, SEC-LLS, elemental analysis, and zeta-potential measurement. Chitosan ethers with different degrees of substitution (DSs) were obtained by adjusting the molar ratio of the etherifying agent to N-acetylglucosamine unit (AGU) of chitosan. The total DS for methyl chitosan (MCh) increased from 1.17 to 2.25, and trimethyl chitosan (TMCh) was obtained with DSN-trimethyl as high as 0.48. The total DS for carboxymethyl chitosan (CMCh) was in the range 0.75-1.45. Both N-substitution and O-substitution were observed, and the eOH groups at C-6 displayed relative higher reactivity than the -OH groups at C-3. In comparison with the traditional methods and solvents, aqueous alkali/urea solutions proved to be a stable and more homogeneous medium for preparing chitosan ethers with higher DS through a one-step reaction.
引用
收藏
页码:138 / 144
页数:7
相关论文
共 41 条
[1]   Preparation, characterization and antibacterial properties of cyanoethylchitosan/cellulose acetate polymer blended films [J].
Abou-Zeid, N. Y. ;
Waly, A. I. ;
Kandile, N. G. ;
Rushdy, A. A. ;
El-Sheikh, M. A. ;
Ibrahim, H. M. .
CARBOHYDRATE POLYMERS, 2011, 84 (01) :223-230
[2]   Synthesis, characterization, cytotoxicity and antibacterial studies of chitosan, O-carboxymethyl and N,O-carboxymethyl chitosan nanoparticles [J].
Anitha, A. ;
Rani, V. V. Divya ;
Krishna, R. ;
Sreeja, V. ;
Selvamurugan, N. ;
Nair, S. V. ;
Tamura, H. ;
Jayakumar, R. .
CARBOHYDRATE POLYMERS, 2009, 78 (04) :672-677
[3]   Alternative Approach to Synthesize Methylated Chitosan Using Deep Eutectic Solvents, Biocatalyst and "Green" Methylating Agents [J].
Bangde, Prachi S. ;
Jain, Ratnesh ;
Dandekar, Prajakta .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2016, 4 (06) :3552-3557
[4]   Unique gelation behavior of cellulose in NaOH/Urea aqueous solution [J].
Cai, J ;
Zhang, L .
BIOMACROMOLECULES, 2006, 7 (01) :183-189
[5]   Synthesis and pH sensitivity of carboxymethyl chitosan-based polyampholyte hydrogels for protein carrier matrices [J].
Chen, LY ;
Tian, ZG ;
Du, YM .
BIOMATERIALS, 2004, 25 (17) :3725-3732
[6]   Application of chitosan, a natural aminopolysaccharide, for dye removal from aqueous solutions by adsorption processes using batch studies: A review of recent literature [J].
Crini, Gregorio ;
Badot, Pierre-Marie .
PROGRESS IN POLYMER SCIENCE, 2008, 33 (04) :399-447
[7]   A novel method for obtaining a quaternary salt of chitosan [J].
de Britto, Douglas ;
Assis, Odilio B. G. .
CARBOHYDRATE POLYMERS, 2007, 69 (02) :305-310
[8]   C-13 AND H-1-NMR SPECTROSCOPY OF CHITOSAN AND N-TRIMETHYL CHLORIDE DERIVATIVES [J].
DOMARD, A ;
GEY, C ;
RINAUDO, M ;
TERRASSIN, C .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 1987, 9 (04) :233-237
[9]  
Dong YM, 2000, J APPL POLYM SCI, V76, P2057, DOI 10.1002/(SICI)1097-4628(20000628)76:14<2057::AID-APP8>3.0.CO
[10]  
2-I