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Preparation method of thermo-sensitive chitosan polymer connected with sugar molecules

A chitosan and temperature-sensitive technology, applied in the field of biological materials and nanomaterials, can solve problems such as single function, and achieve the effects of wide source of raw materials, simple and easy synthesis method, and wide application prospects.

Inactive Publication Date: 2015-03-04
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the chemical structure of chitosan is relatively simple, and its function is relatively simple, so in order to meet higher application requirements, it needs to be modified by physical or chemical methods.

Method used

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  • Preparation method of thermo-sensitive chitosan polymer connected with sugar molecules
  • Preparation method of thermo-sensitive chitosan polymer connected with sugar molecules
  • Preparation method of thermo-sensitive chitosan polymer connected with sugar molecules

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Weigh 0.6 g of CS-Br, dissolve in N,N-dimethylformamide, add MEO 2 MA monomer 5.2 grams, OEGMA monomer 0.3 grams, add catalyst cuprous chloride (80 mg) / pentamethyl divinyl triamine (40 mg) again, system is through vacuumizing-argon process three times, in argon 40 under air protection o C for 18 hours, dialyzed and freeze-dried to obtain CS- g -P(MEO 2 MA- co -OEGMA)-Br. Weigh out 3.6 g CS- g -P(MEO 2 MA- co -OEGMA)-Br, dissolved in N,N-dimethylacetamide, add 2.0 g of HEMA monomer, then add catalyst cuprous chloride (48 mg) / bipyridine (105 mg), the system is vacuum- Nitrogen filling process three times, under the protection of nitrogen at 60 o C for 10 hours, dialyzed and freeze-dried to obtain CS- g -P(MEO 2 MA- co -OEGMA)- b -PHEMA. Weigh out 2.8 g CS- g -P(MEO 2 MA- co -OEGMA)- b -PHEMA, dissolved in N,N-dimethylformamide, added 2.4 grams of propargyl-3-carboxypropionate, 3.2 grams of N,N-dicyclohexylcarbodiimide, 20 o C for 48 hours, suction fi...

Embodiment 2

[0031] Weigh 0.6 g of CS-Br, dissolve in N,N-diethylformamide, add MEO 2 MA monomer 4.8 grams, OEGMA monomer 0.7 grams, add catalyst cuprous bromide (111 mg) / pentamethyl divinyl triamine (40 mg) again, system is through vacuumizing-argon process three times, in argon Under the protection of gas at 45 o C for 16 hours, dialyzed and freeze-dried to obtain CS- g -P(MEO 2 MA- co -OEGMA)-Br. Weigh out 2.4 g CS- g -P(MEO 2 MA- co -OEGMA)-Br, dissolved in N,N-dimethylformamide, add HEMA monomer 1.5 g, then add catalyst cuprous chloride (52 mg) / pentamethyldivinyltriamine (26 mg) , the system was vacuum-filled with argon three times, under the protection of argon at 45 o C for 18 hours, dialyzed and freeze-dried to obtain CS- g -P(MEO 2 MA- co -OEGMA)- b -PHEMA. Weigh out 2.0 g CS- g -P(MEO 2 MA- co -OEGMA)- b -PHEMA, dissolved in N,N-dimethylformamide, added 1.2 grams of propargyl-3-carboxypropionate, 0.9 grams of chlorosulfonic acid, 25 o C for 40 hours, suction...

Embodiment 3

[0033] Weigh 0.6 g of CS-Br, dissolve in N,N-dimethylformamide, add MEO 2 6.0 grams of MA monomer, 1.3 grams of OEGMA monomer, and then add catalyst cuprous bromide (110 mg) / hexamethyltriethylenetetramine (103 mg), and the system is vacuumized-argon-filled three times. Under the protection of air at 50 o C for 12 hours, dialyzed and freeze-dried to obtain CS- g -P(MEO 2 MA- co -OEGMA)-Br. Weigh out 3.9 g CS- g -P(MEO 2 MA- co -OEGMA)-Br, dissolved in N,N-dimethylacetamide, adding 1.8 grams of HEMA monomer, and then adding the catalyst cuprous bromide (48 mg) / bipyridine (108 mg), the system was vacuum- Argon filling process three times, under the protection of argon at 55 o C for 12 hours, dialyzed and freeze-dried to obtain CS- g -P(MEO 2 MA- co -OEGMA)- b -PHEMA. Weigh out 3.2 g CS- g -P(MEO 2 MA- co -OEGMA)- b -PHEMA, dissolved in N,N-diethylformamide, added 1.3 grams of propargyl-3-carboxypropionate, 1.0 grams of thionyl chloride, 30 o C for 32 hours, ...

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Abstract

The invention belongs to the field of biological materials and nano-materials and particularly relates to a preparation method of a thermo-sensitive chitosan polymer connected with sugar molecules. The method comprises the specific steps of initiating atom transfer radical polymerization (ATRP) of 2-(2-methoxyethoxy) ethylmethacrylate (MEO2MA) and oligo(ethylene glycol) methacrylate (OEGMA) by taking a chitosan bromide (CS-Br) as a macroinitiator to obtain CS-g-P(MEO2MA-co-OEGMA)-Br; initiating the ATRP of hydroxyethyl methacrylate (HEMA) by taking the CS-g-P(MEO2MA-co-OEGMA)-Br as the macroinitiator to obtain CS-g-P(MEO2MA-co-OEGMA)-poly(2-hydroxyethyl methacrylate (PHEMA); performing esterification reaction and click chemistry to obtain a thermo-sensitive copolymer of which chitosan serves as a main chain and galactose is grafted. The polymer has biocompatibility, biodegradability, thermo-sensibility and liver targeting, and the polymer in a water solution can be self-assembled to form micelle, and has a wide application prospect in the fields of medicine controlled release, targeted therapy, biosensors and the like. The preparation method is simple and easy to operate, and has a great popularization and application value. Raw materials can be industrially produced.

Description

technical field [0001] The invention belongs to the field of biological materials and nanometer materials, and in particular relates to a preparation method of a chitosan temperature-sensitive copolymer connected with sugar molecules. Background technique [0002] Chitosan is a natural biopolysaccharide with good biocompatibility and biodegradability, and is widely used in medicine, food, cosmetics and many other fields. However, the chemical structure of chitosan is relatively simple, and its function is relatively simple, so in order to meet higher application requirements, it needs to be modified by physical or chemical methods. Dong et al. (Feng H., Dong C. M.. Biomacromolecules , 2006, 7, 3069) with Sn(Oct) 2 As a catalyst, a branched chitosan graft copolymer of polylactic acid was prepared by ring-opening polymerization (Ring Opening Polymerization, ROP); Bai et al. (Li, N., Bai, R. B., Liu C. K.. Langmuir , 2005, 21, 11780) used reversible addition-fragmentation c...

Claims

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Application Information

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IPC IPC(8): C08F285/00C08F251/00C08F220/28C08F8/02
Inventor 袁伟忠邹辉
Owner TONGJI UNIV
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