(2-羟基-3-脱氢枞氧基)丙基羟乙基壳聚糖制备及性能研究

doi:10.13218/j.cnki.csdc.2018.04.003

Abstract

Abstract: A nonionic polymeric surfactant (2-hydroxyl-3-dehydrofiroxy) propyl hydroxyethyl chitosan (DAGE-g-HECTS) was prepared with the raw materials of dehydroabietyl glycidyl ether and N,O-hydroxyethyl chitosan.FT-IR、¹H NMR and grafting degree (DG) of DAGE-g-HECTS was determined.The surface activity of DAGE-g-HECTS and its variation with the DG were investigated by using surface tension method.The emulsifying property of DAGE-g-HECTS was evaluated according to the stability time of emulsion composed of water and benzene with DAGE-g-HECTS as emulsifying agent.Results indicate that the target product is successfully prepared.The critical micelle concentration (cmc) of DAGE-g-HECTS in aqueous solution decreases from 1.080 6 to 0.247 2 g/L with the increase of DG from 17.78% to 44.31%,but the minimum surface tension ( γ_min) of DAGE-g-HECTS can reach approximately 36.2 mN/m in aqueous solution.The stability time of emulsion composed of water and benzene with DAGE-g-HECTS as emulsifying agent extends with the increase of DG.When the DG of DAGE-g-HECTS is 23.16%,the stability time of emulsion is 348 s,which is longer than that with AEO-9 as emulsifying agent (327 s),and when the DG of DAGE-g-HECTS is 40.45%,the stability time of emulsion is 712 s,which is longer than that with Tween-60 as emulsifying agent (653 s).

Key words: nonionic surfactant, dehydroabietyl glycidyl ether, hydroxyethyl chitosan, surface activity, emulsi-fying property

CLC Number:

TQ423.2

WANG Ting, ZHANG Ting-ting, CAI Zhao-sheng, SANG Shu-min, HE Jian-ling, WANG Yi-ning. Synthesis and performance of (2-hydroxyl-3-dehydrofiroxy) propyl hydroxyethyl chitosan[J].China Surfactant Detergent & Cosmetics, 2018, 48(4): 196-200.

References

[1]Liu H,Zhao Y,Cheng S,et al.Syntheses of novel chitosan derivative with excellent solubility,anticoagulation,and antibacterial property by chemical modification [J].Journal of Applied Polymer Science,2012,124:2641-2648.
[2] Dash M,Chiellini F,Ottenbrite R M,et al.Chitosan—a versatile semi-synthetic polymer in biomedical applications [J].Progress in Polymer Science,2011,36:981-1014.
[3] Shao K,Han B,Gao J,et al.Synthesis and characterization of a hydroxyethyl derivative of chitosan and evaluation of its biosafety [J].Journal of Ocean University of China (Oceanic and Coastal Sea Research),2015,14(4):703-709.
[4] Xu X,Zhuang X,Cheng B,et al.Manufacture and properties of cellulose/O-hydroxyethyl chitosan blend fibers [J].Carbohydrate Polymers,2010,81:541-544.
[5] Li M,Han B,Liu W.Preparation and properties of a drug release membrane of mitomycin C with N-succinyl-hydroxyethyl chitosan [J].Journal of Materials Science:Materials in Medicine,2011,22:2745-2755.
[6] Xu Jing,Zhou Xueqing,Yao Kangde,et al.Synthesis and properties of water-soluble glycolchitosan [J].Chemical Research and Application,2004,16(2):225-226.
[7] Liu Shengli,Li Xiaofeng,Shu Yong,et al.Synthesis and characterization of water soluble O-hydroxyethyl chitosan graft polylactic acid [J].Oethopaedic Biomechanics Materials and Clinical Study,2013,10(2):5-9.
[8] Shao K,Han B,Dong W,et al.Pharmacokinetics and biodegradation performance of a hydroxypropyl chitosan derivative [J].Journal of Ocean University of China (Oceanic and Coastal Sea Research),2015,14:888-896.
[9] Li H,Huo M,Zhou J,et al.Enhanced oral absorption of paclitaxel in N-deoxycholic acid-N,O-hydroxyethyl chitosan micellar system [J].Journal of Pharmaceutical Sciences,2010,99:4543-4553.
[10] Huo M,Liu Y,Wang L,et al.Redox-sensitive micelles based on O,N-hydroxyethyl chitosan-octylamine conjugates for triggered intracellular delivery of paclitaxel [J].Molecular Pharmaceutics,2016,13:1750-1762.
[11] Spinner J L,Oberoi H S,Yorgensen Y M,et al.Methylglycol chitosan and a synthetic TLR4 agonist enhance immuneresponses to influenza vaccine administered sublingually [J].Vaccine,2015,33:5845-5853.
[12] Song Zhanqian.Oleoresin charateristics and chemical classification of pinus [M].Hefei:Press of University of Science and Technology of China,2009:31-118.
[13] Jiang Shimeng,Cai Zhaosheng,Chen Zhidong,et al.The synthesis of dehydroabietyl glycidyl ether and its optimization of condition [J].Chemical World,2014,55:401-405.
[14] Cai Zhaosheng,Jiang Shimeng,Zhu Xuemei,et al.(2-hydroxyl-3-dehydrofiroxy) propyl chitooligosaccharide and its manufacturing method:103965373 B [P].2016-02-24.
[15] Duan W,Chen C,Jiang L,et al.Preparation and characterization of the graft copolymer of chitosan with poly[rosin-(2-acryloyloxy)ethyl ester] [J].Carbohydrate Polymers,2008,73:582.
[16] Qi F,Cai Z S,Zhu X M,et al.Synthesis,characterization,and performance of a novel polymeric cationic surfactant based on low molecular weight chitosan and 3-chloro-2-hydroxypropyl dimethyl dehydro-abietyl ammonium chloride (CHPDMDHA) [J].Journal of Surfactants and Detergents,2015,18(3):463-470.
[17] Cai Zhaosheng,Qi Fan,Zhu Xuemei,et al.(2-hydroxyl-3-dehydroabioxy) propyl hydroxyethyl chitosan and its manufacturing method:103923228 B [P].2016-02-10.

Synthesis and performance of (2-hydroxyl-3-dehydrofiroxy) propyl hydroxyethyl chitosan

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