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Chitosan derivative hydrogel and preparation method and application thereof

A technology of chitosan derivatives and hydrogels, which can be used in pharmaceutical formulations, drug delivery, medical preparations of non-active ingredients, etc., can solve the problems of hydrogels without temperature sensitivity, and achieve increased water solubility and huge The effect of applying the foreground

Active Publication Date: 2016-04-20
GUANGDONG PROV MEDICAL INSTR INST
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The patent (Chinese Publication No. CN104479150A) discloses a method for preparing a multi-cross-linked polysaccharide injectable hydrogel. The hydrogel is obtained by reacting polysaccharide polymers modified by aldehydes with chitosan, but the water Gels are not thermosensitive
The patent (Chinese Publication No. CN104258426A) discloses an injectable pH-sensitive self-healing hydrogel, which is composed of chitosan and polyethylene glycol with both ends of the aldehydization. In situ gels can be formed by mixing, but temperature sensitivity of the gels is not addressed

Method used

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  • Chitosan derivative hydrogel and preparation method and application thereof
  • Chitosan derivative hydrogel and preparation method and application thereof
  • Chitosan derivative hydrogel and preparation method and application thereof

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preparation example Construction

[0030] The preparation method of the chitosan derivative hydrogel corresponding to the above structural formula may further comprise the steps:

[0031] 1) Dissolving fatty alcohol polyether in a solvent, adding dimethyl sulfoxide, pyridine and trifluoroacetic acid, mixing evenly at 0-5°C, and fully reacting;

[0032] 2) adding dicyclohexylcarbodiimide, fully reacting at room temperature to obtain fatty alcohol polyether with acetaldehyde terminal;

[0033] 3) dissolving the fatty alcohol polyether and chitosan of the terminal acetaldehyde group in a mixed solvent, adding an aqueous solution of sodium cyanoborohydride, and fully reacting to obtain a chitosan derivative with a side chain containing a fatty alcohol polyether structure;

[0034] 4) adding water to the chitosan derivatives containing fatty alcohol polyether structure in the side chain to obtain hydrogel.

[0035] Preferably, the preparation method of the chitosan derivative hydrogel corresponding to the above str...

Embodiment 1

[0052] 40g fatty alcohol polyoxyethylene ether AEO-3 (molecular formula: H-(O-CH 2 CH 2 ) 3 -O-C 12 h 25) was dissolved in 100mL of dichloromethane, 160g of dimethyl sulfoxide was added, and the temperature was kept at 0-5°C in an ice-water bath, then 24g of pyridine and 33.6g of trifluoroacetic acid were added, stirred at a constant temperature of 0-5°C for 1 hour, and then added 31.6g of dicyclohexylcarbodiimide, reacted at room temperature for 24 hours, filtered to remove dicyclohexylurea after the reaction was completed, and distilled under reduced pressure. The obtained solid was mixed with acrylonitrile and methyl butyl ether 5:1 (weight ratio) The system is recrystallized and then dried to obtain fatty alcohol polyoxyethylene ether with acetaldehyde terminal. Dissolve 1g of fatty alcohol polyoxyethylene ether with acetaldehyde terminal group and 25g of chitosan in 400mL of mixed solvent of acetic acid and methanol (acetic acid:methanol=0.5:1, volume ratio), and use ...

Embodiment 2

[0055] 25g oleyl alcohol polyoxyethylene ether OE-20 (molecular formula: H-(O-CH 2 CH 2 ) 20 -O-C 18 h 35 ) was dissolved in 100mL of dichloromethane, 25g of dimethyl sulfoxide was added, and the temperature was kept at 0-5°C in an ice-water bath, then 0.75g of pyridine and 1.0g of trifluoroacetic acid were added, and the reaction was stirred at a constant temperature of 0-5°C for 1 hour, then Add 1.5g of dicyclohexylcarbodiimide, react at room temperature for 24 hours, remove dicyclohexylurea by filtration after the reaction is completed, and distill under reduced pressure. The mixed system is recrystallized and then dried to obtain fatty alcohol polyether with acetaldehyde terminal. Dissolve 1g of fatty alcohol polyether with acetaldehyde terminal group and 0.28g of chitosan in 60mL of mixed solvent of acetic acid and ethanol (acetic acid:ethanol=2:1, volume ratio), and use 0.5mol / L sodium hydroxide solution Adjust the pH value of the mixed system to pH=5, then add 18 m...

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Abstract

The invention discloses chitosan derivative hydrogel and a preparation method and application thereof. A chitosan derivative has a structural formula (please see the formula in the description); in the formula, m is any natural number from 930 to 1550, n is any natural number from 2 to 19, and R is C8-C18 straight-chain hydrocarbon. The preparation method of the hydrogel includes the following steps of firstly, dissolving fatty alcohol polyether in solvent, adding dimethylsulfoxide, adding pyridine and trifluoroacetic acid, and conducting a sufficient reaction; secondly, adding dicyclohexylcarbodiimide to obtain fatty alcohol polyether with glyoxyl at the tail end; thirdly, dissolving the product in the second step and chitosan in mixed solvent, and adding sodium cyanoborohydride to obtain the chitosan derivative with a fatty alcohol polyether structure on a side chain; fourthly, adding water to the chitosan derivative in the third step to obtain the hydrogel. The hydrogel has temperature sensitivity, is in a sol state at a low temperature and in a gel state at a high temperature, can be used as injectable type hydrogel, and can be used for preparing a medical filling material and a medical releasing system.

Description

technical field [0001] The invention relates to a chitosan derivative hydrogel, a preparation method and application thereof. Background technique [0002] Hydrogel is a kind of network structure material with high water content but insoluble in water. As a soft water-based material, hydrogel has good biocompatibility. Therefore, this type of material has been widely used in many fields such as food, cosmetics, and medicine. Among the hydrogels, there is a class of hydrogels with temperature sensitivity, such as poly(N-isopropylacrylamide) (PNIPAM) hydrogels, which swell when the temperature is lower than 25 °C and shrink when the temperature is higher than 25 °C. . The tri-block copolymer PEO-PPO-PEO (trade name Poloxamers) is also temperature sensitive. As the temperature changes, the material will undergo sol and gel state transitions. Materials with this feature can be used as injectable water When used as a gel, the material is in a sol state in vitro and forms a gel...

Claims

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Application Information

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IPC IPC(8): C08J3/075C08B37/08A61L27/20A61L27/52A61L27/50A61K47/36A61K9/06
CPCA61K9/0019A61K9/06A61K47/36A61L27/20A61L27/50A61L27/52A61L2400/06C08B37/003C08J3/075
Inventor 刘群峰陈军耿志杰张泽荣张锦
Owner GUANGDONG PROV MEDICAL INSTR INST
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