Preparation of Hydrogels Based on Dehydroabietyl Polyoxyethylene Glycidyl Ether Grafted Hydroxyethyl Chitosan and Their Properties

doi:10.19894/j.issn.1000-0518.210452

Chinese Journal of Applied Chemistry ›› 2022, Vol. 39 ›› Issue (9): 1421-1428.DOI: 10.19894/j.issn.1000-0518.210452

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Preparation of Hydrogels Based on Dehydroabietyl Polyoxyethylene Glycidyl Ether Grafted Hydroxyethyl Chitosan and Their Properties

Xu-Juan HUANG¹, Ting WANG¹, Zheng-Qing DING¹, Xin-Xin YANG¹^,², Zhao-Sheng CAI¹(), Shi-Bing SHANG²

^1.School of Chemistry and Chemical Engineering，Yancheng Institute of Technology，Yancheng 224051，China
^2.Institute of Chemical Industry of Forest Products，Chinese Academy of Forestry，Nanjing 210042，China

Received:2021-09-05 Accepted:2022-05-05 Published:2022-09-01 Online:2022-09-08
Contact: Zhao-Sheng CAI
About author:jsyc-czs@163.com
Supported by:
the National Natural Science Foundation of China(32071706);the Jiangsu Provincial Key Lab of Bioenergy and Biomaterial Fund(JSBEM201909)

Abstract

Abstract:

Dehydroabietol polyoxyethylene（10） ether （DA（EO）₁₀H） is condensated with epichlorohydrin in the presence of boron fluoride diethyl etherate firstly， and then dehydroabietyl polyoxyethylene glycidyl ether （DA（EO）₁₀GE） is obtained through dehydrochlorination of the condensation product in the presence of NaOH. DA（EO）₁₀GE grafted hydroxyethyl chitosan （DA（EO）₁₀GE-g-HECTS） is prepared through grafting DA（EO）₁₀GE to hydroxyethyl chitosan （HECTS）. The hydrogels based on DA（EO）₁₀GE-g-HECTS are prepared through cross-linking reaction between Genipin and DA（EO）₁₀GE-g-HECTSs. The increase of molar ratio of DA（EO）₁₀GE versus sugar unit could result in the increase of grafting degree （DG） of DA（EO）₁₀GE-g-HECTSs， the gelation time of DA（EO）₁₀GE-g-HECTS/Genipin with high DG is longer than that with low DG， and increasing the Genipin amount could improve the capability of DA（EO）₁₀GE-g-HECTS/Genipin to form hydrogel. The relation between the cumulative release rate of Chloramphenicol loaded in DA（EO）₁₀GE-g-HEC/GE gel and times in artificial intestinal fluid could be well described by Boltzmann function， and the final cumulative release rate could be improved by increasing the DG or decreasing the Genipin dosage. The release behavior of drug loaded in the hydrogel which is formed by the cross-linking reaction between DA（EO）₁₀GE-g-HECTS with low DG and Genipin accords with the characteristics of first-order kinetic equation.

Key words: Hydroxyethyl chitosan, Dehydroabietyl polyoxyethylene glycidyl ether, Hydrogels, Drug release

CLC Number:

O636.1

Xu-Juan HUANG, Ting WANG, Zheng-Qing DING, Xin-Xin YANG, Zhao-Sheng CAI, Shi-Bing SHANG. Preparation of Hydrogels Based on Dehydroabietyl Polyoxyethylene Glycidyl Ether Grafted Hydroxyethyl Chitosan and Their Properties[J]. Chinese Journal of Applied Chemistry, 2022, 39(9): 1421-1428.

Figures/Tables 8

References 23

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样品 Sample	DA（EO）₁₀GE?g?HECTS水溶液体积 V（DA（EO）₁₀GE?g?HECTS）/mL	Genipin水溶液体积V（Genipin）/mL	凝胶时间 Gelation time/min
A?1	0.70	0.70	190
A?2	1.0	0.50	255
A?3	0.90	0.30	325
A?4	1.0	0	-
B?1	0.70	0.70	310
B?2	1.0	0.50	415
B?3	0.90	0.30	620
B?4	1.0	0	-

样品 Sample	DA（EO）₁₀GE?g?HECTS水溶液体积 V（DA（EO）₁₀GE?g?HECTS）/mL	Genipin水溶液体积V（Genipin）/mL	凝胶时间 Gelation time/min
A?1	0.70	0.70	190
A?2	1.0	0.50	255
A?3	0.90	0.30	325
A?4	1.0	0	-
B?1	0.70	0.70	310
B?2	1.0	0.50	415
B?3	0.90	0.30	620
B?4	1.0	0	-

凝胶样品 Sample of hydrogel	拟合方法 Fitting method	拟合方程 Fitting function	相关系数 Correlation coefficients
凝胶1 Hydrogel 1	ExpDec1 fitting	F= -65.68134×exp（-1.02973t）+65.61714	0.999 53
凝胶1 Hydrogel 1	Boltzmann fitting	F=65.46377-260.13986/（1+exp（1.13852×（t+1.40913）））	0.999 6
凝胶2 Hydrogel 2	ExpDec1 fitting	F= -86.64533×exp（-t/1.61829）+83.04387	0.954 26
凝胶2 Hydrogel 2	Boltzmann fitting	F=80.02709-88.32926/（1+exp（1.77535×（t-1.27134）））	0.999 4
凝胶3 Hydrogel 3	ExpDec1 fitting	F= -73.97387×exp（-t/1.02993）+73.67559	0.998 18
凝胶3 Hydrogel 3	Boltzmann fitting	F= 73.11953-163.5847/（1+exp（1.32674×（t+0.16049）））	0.999 81

凝胶样品 Sample of hydrogel	拟合方法 Fitting method	拟合方程 Fitting function	相关系数 Correlation coefficients
凝胶1 Hydrogel 1	ExpDec1 fitting	F= -65.68134×exp（-1.02973t）+65.61714	0.999 53
凝胶1 Hydrogel 1	Boltzmann fitting	F=65.46377-260.13986/（1+exp（1.13852×（t+1.40913）））	0.999 6
凝胶2 Hydrogel 2	ExpDec1 fitting	F= -86.64533×exp（-t/1.61829）+83.04387	0.954 26
凝胶2 Hydrogel 2	Boltzmann fitting	F=80.02709-88.32926/（1+exp（1.77535×（t-1.27134）））	0.999 4
凝胶3 Hydrogel 3	ExpDec1 fitting	F= -73.97387×exp（-t/1.02993）+73.67559	0.998 18
凝胶3 Hydrogel 3	Boltzmann fitting	F= 73.11953-163.5847/（1+exp（1.32674×（t+0.16049）））	0.999 81

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Preparation of Hydrogels Based on Dehydroabietyl Polyoxyethylene Glycidyl Ether Grafted Hydroxyethyl Chitosan and Their Properties

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