Intelligent thermo-sensitive glycosyl hydrogel with dumbbell structure and preparation method of hydrogel

A thermosensitive, hydrogel technology, applied in the field of dumbbell structure thermosensitive sugar-based smart hydrogel and its preparation, can solve the problems of low stimulus response sensitivity and poor stability, and achieve the effect of good biocompatibility

Inactive Publication Date: 2013-02-27
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to overcome the defects of poor stability of small-molecule supramolecular gels and low sensitivity of polymer hydrogels to stimuli and respond to them, and prepare a smart hydrogel with dumbbell structure with controllable structure of sugar groups introduced into the molecules

Method used

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  • Intelligent thermo-sensitive glycosyl hydrogel with dumbbell structure and preparation method of hydrogel
  • Intelligent thermo-sensitive glycosyl hydrogel with dumbbell structure and preparation method of hydrogel

Examples

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Embodiment 1

[0029] Synthesis of allyl diacetone glucose: In a 250 mL four-neck flask equipped with a thermometer reflux condenser, add 150 mL of dry anhydrous acetone and 9.0 g (0.05 mol) of crushed and dried glucose, add catalyst anhydrous FeCl 3 (1.7g, 0.01mol). Reflux reaction under ultrasonic conditions for 2h. Then dilute Na 2 CO 3 Solution 300 ml, CHCl 3 Extract three times (50 ml×3), combine the organic phases and wash with saturated brine (50 ml×3), wash with anhydrous Na 2 SO 4 Dry, filter and distill under reduced pressure to obtain a crude product with a yield of 75.8%. Recrystallize with cyclohexane to obtain white crystalline diacetone glucose DAG. In a 250mL dry and clean three-necked flask, add DAG (10 g, 0.04mol) and 80mL dry tetrahydrofuran and stir to dissolve. Under nitrogen protection, add 60% sodium hydride (2.4g, 0.052 mol), and then The reaction was stirred for 1 h, and allyl bromide (5.45 g, 0.045 mol) was slowly added dropwise. After the addition was complet...

Embodiment 2

[0033] The difference from Example 1 is: in a 250 mL four-necked flask equipped with a thermometer, add 100 ml of tetrahydrofuran, then add 5.0 g of 3-allyl diacetone glucose and 0.2 g of dimethylbenzyl dithiobenzoate g, under the protection of nitrogen, add 0.05 g of initiator azobisisobutyronitrile AIBN, react for 2 hours in a water bath at 70 ° C, and use TLC to detect that the polymerization of the allyl sugar-based monomer is complete; then add the comonomer N- Propyl acrylamide 10.0 g was continued to polymerize at 70°C for 5 h, and the reaction was detected by TLC until the monomer basically disappeared; 5.0 g of allyl diacetone glucose dissolved in 50 mL of tetrahydrofuran was added by steel needle transfer method, and the polymerization was continued for 5 h. Add 2 mol / L hydrochloric acid to hydrolyze the deprotected acetone, hydrolyze for 2 hours, precipitate with methanol, and dry to obtain 15.3 g of “glycosyl-N-propylacrylamide-glycosyl” dumbbell structure glycosyl ...

Embodiment 3

[0035] The difference from Example 1 is: in a 250 mL four-necked flask equipped with a thermometer, add 100 ml of tetrahydrofuran, then add 5.0 g of 3-allyl diacetone glucose and 0.2 g of dimethylbenzyl dithiobenzoate g, under the protection of nitrogen, add 0.05 g of initiator azobisisobutyronitrile AIBN, react for 2 hours in a water bath at 70 ° C, and use TLC to detect that the polymerization of allyl sugar-based monomers is complete; then add comonomer N, 10.0 g of N-diethylacrylamide, continue to polymerize at 70 ° C for 5 h, TLC detects the reaction until the monomer basically disappears; add 5.0 g of allyl diacetone glucose dissolved in 50 mL of tetrahydrofuran by steel needle transfer method, and continue to polymerize 5h. Add 2 mol / L hydrochloric acid to hydrolyze the deprotected acetone, hydrolyze for 2 hours, precipitate with methanol, and dry to obtain 16.4 g of “glycosyl-N,N-diethylacrylamide-glycosyl” dumbbell structure glycosyl hydrogel.

[0036] The structure ...

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Abstract

The invention relates to intelligent thermo-sensitive glycosyl hydrogel with a dumbbell structure and a preparation method of the hydrogel. The whole structure of the hydrogel is dumbbell-shaped, small molecular chondroitin sulfate proteoglycans are used as raw materials in preparation, a glycosyl monomer containing polymerizable double bonds is firstly synthesized by means of esterification and etherification reaction, and then double thioester serving as a chain transfer agent is polymerized with an N-alkyl acrylamide thermo-sensitive monomer by a reversible addition fragmentation chain transfer agent free radical polymerization method to prepare the novel intelligent glycosyl hydrogel with the dumbbell structure. The hydrogel has the advantages that the structure can be controlled, the molecular weight of the hydrogel is between that of supramolecular gel and that of polymer gel, the shortcomings of the supramolecular gel and the polymer gel are overcome, carbohydrates are used as raw materials, and the hydrogel serving as a natural biomass resource has fine biocompatibility, biodegradability, non-toxicity, no stimulation and the like that petrochemical raw materials do not have.

Description

technical field [0001] The invention relates to a temperature-sensitive sugar-based intelligent hydrogel with a dumbbell structure and a preparation method thereof. Background technique [0002] Gel is a common "soft matter" with a three-dimensional network structure similar to viscoelastic liquids or solids. According to the composition of the gel, it can be divided into supramolecular gel and polymer gel; according to the cross-linking method, it can be divided into physical gel and chemical gel; according to the classification of medium, the gel can also be divided into organic gel, hydrogel and aerogel. Gels, which are classified in detail as figure 1 shown. Among them, the hydrogel formed with water as the medium exists widely no matter in nature or artificially synthesized. The water content in organisms is 70-80%, and it can be regarded as a complex hydrogel system, ranging from cells, tissues, to organs. Therefore, the study of hydrogels is of great significance...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F293/00C08F2/38C08F220/54
Inventor 朱金丽汤艳峰孙同明陈玥竹朱国华张素梅项蕊高鹏飞
Owner NANTONG UNIVERSITY
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