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Method for preparing dual-sensitivity graft copolymer with chitosan as main chain

A technology of graft copolymer and chitosan, which is applied in the fields of polymer materials and biomedical engineering, can solve problems such as single function, poor solubility, and failure to meet application requirements, and achieve the effect of wide sources and simple and easy synthesis methods

Inactive Publication Date: 2009-11-18
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the structure of chitosan is relatively simple, the function is relatively single, and the solubility is poor, which cannot meet higher application requirements. Therefore, it needs to be modified by physical and chemical methods to expand its function.

Method used

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  • Method for preparing dual-sensitivity graft copolymer with chitosan as main chain

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Weigh 5 grams of chitosan, disperse and dissolve it with N,N-dimethylformamide, add 15 grams of triethylamine, add 30 grams of 2-bromoisobutyryl bromide dropwise at 0°C, and drop it in 20 minutes. And react at 10°C for 72 hours. After desalination by suction filtration, precipitation with deionized water, and vacuum drying, a bromine-terminated chitosan macromolecular initiator was obtained. Weigh 0.5 g of bromo-terminated chitosan macroinitiator and dissolve it in N,N-dimethylformamide, add methacrylic acid-N,N-dimethylaminoethyl ester 3 g, then add initiator bromination Cuprous (80 mg) / hexamethyltriethylenetetramine (150 mg) was vacuum-filled three times with nitrogen, and reacted in an oil bath at 20° C. for 48 hours under nitrogen protection. The product was dialyzed with deionized water and freeze-dried to obtain a double-sensitive graft copolymer with chitosan as the main chain.

[0020] The representative structural formula of the dual-sensitivity graft copolym...

Embodiment 2

[0022] Weigh 5 grams of chitosan, disperse and dissolve it with N, N-dimethylformamide, add 20 grams of diethylamine, add 40 grams of 2-bromopropionyl bromide dropwise at 5 ° C, drop it in 30 minutes, and The reaction was carried out at 15°C for 60 hours. After desalination by suction filtration, precipitation with deionized water, and vacuum drying, a bromine-terminated chitosan macromolecular initiator was obtained. Weigh 0.5 g of bromo-terminated chitosan macroinitiator and dissolve it in N,N-dimethylacetamide, add methacrylic acid-N,N-dimethylaminoethyl 4 g, then add the initiator for chlorination Cuprous (90 mg) / bipyridine (160 mg) was vacuum-filled three times with nitrogen, and reacted in an oil bath at 40° C. for 36 hours under nitrogen protection. The product was dialyzed with deionized water and freeze-dried to obtain a double-sensitive graft copolymer with chitosan as the main chain.

Embodiment 3

[0024] Weigh 5 grams of chitosan, disperse and dissolve it with N,N-dimethylacetamide, add 18 grams of pyridine, add 36 grams of 2-bromoisobutyryl bromide dropwise at 8°C, drop it in 40 minutes, and The reaction was carried out at 20°C for 48 hours. After desalination by suction filtration, precipitation with deionized water, and vacuum drying, a bromine-terminated chitosan macromolecular initiator was obtained. Weigh 0.5 g of bromo-terminated chitosan macroinitiator and dissolve it in N, N-diethylformamide, add methacrylic acid-N, N-dimethylaminoethyl 6 g, then add initiator bromination Cuprous (100 mg) / bipyridine (180 mg) was vacuum-filled three times with nitrogen, and reacted in an oil bath at 50° C. for 10 hours under nitrogen protection. The product was dialyzed with deionized water and freeze-dried to obtain a double-sensitive graft copolymer with chitosan as the main chain.

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Abstract

The invention belongs to the field of polymer material and biomedical engineering and particularly relates to a method for preparing dual-sensitivity amphipathic graft copolymer with chitosan as the main chain. The method comprises the following steps: with the protection of inert gases such as nitrogen and argon, hydroxide group or aminogroup in chitosan main chain are adopted to carry out esterification reaction with bromine-containing compound; the hydroxide group or aminogroup are converted into the bromine group; then the bromine group is taken as macroinitiator to polymerize atomic transfer radical of methacrylic acid-N and N-dimethylamino-ethyl methylacrylate monomer to form polymer featuring dual sensitivity of temperature and pH value, thus finally obtaining the dual-sensitivity graft copolymer with chitosan as the main chain. The dual-sensitivity graft copolymer with chitosan as the main chain is provided with biological degradability, biocompatibility, biological activity and pH value sensibility, can be automatically assembled into stable nano micelle in water, thus enjoying wide application in fields such as drug controlled release carrier, soft tissue engineering support material, immunoassay, memory element switch, biosensor and the like. The synthetic method of the invention is simple and feasible, the raw materials can all be applied to industrialized production, thus enjoying very good value in popularization and application.

Description

technical field [0001] The invention belongs to the fields of polymer materials and biomedical engineering, and in particular relates to a preparation method of a dual-sensitive graft copolymer with chitosan as the main chain. Background technique [0002] Chitosan is one of the most abundant natural biopolymer materials with the most abundant reserves in nature. It is obtained by deacetylation of chitin. It has excellent biocompatibility, biodegradability and biological activity, and is called the "sixth element of life". However, the structure of chitosan is relatively simple, the function is relatively single, and the solubility is poor, which cannot meet higher application requirements. Therefore, it needs to be modified by physical and chemical methods to expand its function. prepared by ring-opening polymerization Chitosan graft copolymers with branched chains of polylactide and polycaprolactone were studied. Bai (Li, N.; Bai, R.B.; Liu, C.K. Langmuir, 2005, 21, 1178...

Claims

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Application Information

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IPC IPC(8): C08F251/00C08B37/08
Inventor 袁伟忠赵正达李肖飞顾书英任杰
Owner TONGJI UNIV
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