Preparation method of reactive type water-solubility chitosan derivative

A technology of water-soluble chitosan and derivatives, which is applied in the field of preparation of reactive water-soluble chitosan derivatives, can solve problems such as increased cost, complicated preparation methods, and severe reaction conditions, so as to save raw materials and costs, reduce The effect of simple production cost and equipment

Inactive Publication Date: 2011-09-28
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of these methods is that the degree of substitution of the water-soluble chitosan derivative obtained is relatively low, the reaction time is longer, and the degree of substitution of the prepared chitosan derivative is not easy to control, because the introduced group is not very hydrophilic. , making the water solubility of the derivatives poor
[0006] 1. The preparation method is complex and requires a catalyst, and the post-processing is troublesome, which increases the cost;
[0007] 2. The use of organic solvents not only increases the cost, but also introduces toxic substances, which reduces the biomedical application value of chitosan derivatives;
[0008] 3. The reaction conditions are violent and harsh, and it is not easy to control;
[0009] 4. The prepared water-soluble chitosan derivatives have a low degree of substitution and poor water solubility;
[0010] 5. The preparation process consumes a lot of energy, and the post-processing causes secondary pollution, which does not conform to the concept of environmental protection

Method used

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  • Preparation method of reactive type water-solubility chitosan derivative
  • Preparation method of reactive type water-solubility chitosan derivative
  • Preparation method of reactive type water-solubility chitosan derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 2.0g chitosan (degree of deacetylation DP=90%, weight average molecular weight Mw=500,000) into 100mL aqueous solution containing 1wt% of 2-acrylamide-2-methylpropanesulfonic acid, stir at room temperature for 0.5 hour, Then add p-hydroxyanisole accounting for 1% of the moles of 2-acrylamide-2-methylpropanesulfonic acid to the above solution, continue stirring at room temperature for 0.5 hours, raise the temperature to 50°C, react for 4 hours, filter and cool, Rotary evaporation to 30mL, then placed in a dialysis bag for dialysis for 48 hours, freeze-dried for 24 hours to obtain a white powdery chitosan derivative with a degree of substitution of 0.6. Its structural formula is as follows.

[0032]

[0033] Among them, R=HO 3 SCH 2 C(CH3) 2 NHCOCH=CH 2 , x is 0.9.

[0034] The aqueous solution of the chitosan derivative with a concentration of 0.1wt% is prepared, which has an absorption peak at ultraviolet 236nm.

Embodiment 2

[0036] Add 2.0g of chitosan (degree of deacetylation DP=50%, weight average molecular weight Mw=1,000,000) into 100mL of 2-acrylamide-2-methylpropanesulfonic acid 4wt% aqueous solution, stir at room temperature for 0.5 hours, Then add 2-acrylamide-2-methylpropanesulfonic acid molar p-hydroxyanisole to the above solution, continue stirring at room temperature for 0.5 hours, raise the temperature to 55°C, react for 3 hours, filter and cool, Rotary evaporation to 30mL, then placed in a dialysis bag for dialysis for 48 hours, freeze-dried for 24 hours to obtain a white powdery chitosan derivative with a degree of substitution of 0.7. Its structural formula is as follows.

[0037]

[0038] Among them, R=HO 3 SCH 2 C(CH3) 2 NHCOCH=CH 2 , x is 0.5.

[0039] The aqueous solution of chitosan derivative with a concentration of 0.1wt% is prepared, which has an absorption peak at ultraviolet 240nm.

Embodiment 3

[0041]Add 2.0g chitosan (degree of deacetylation DP=70%, weight average molecular weight Mw=5,000) into 100mL aqueous solution containing 2wt% of 2-acrylamide-2-methylpropanesulfonic acid, stir at room temperature for 0.5 hours, Then add p-hydroxyanisole accounting for 1% of the moles of 2-acrylamide-2-methylpropanesulfonic acid to the above solution, continue stirring at room temperature for 0.5 hours, raise the temperature to 45°C, react for 2 hours, filter and cool, Rotary evaporation to 30mL, then placed in a dialysis bag for dialysis for 48 hours, freeze-dried for 24 hours to obtain a white powdery chitosan derivative with a degree of substitution of 0.3. Its structural formula is as follows.

[0042]

[0043] Among them, R=HO 3 SCH 2 C(CH3) 2 NHCOCH=CH 2 , x is 0.7.

[0044] Aqueous solution with a concentration of 0.1wt% chitosan derivative is prepared, which has absorption peak at ultraviolet 234nm.

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Abstract

The invention relates to a preparation method of a reactive type water-solubility chitosan derivative, which comprises the steps of adding chitosan into the aqueous solution of 2-acrylamido-2-methylpropanesulfonic acid, stirring for 0.5 hour at room temperature, preparing the chitosan aqueous solution to 2 wt% with the mole number of the 2-acrylamido-2-methylpropanesulfonic acid being 0.5-4 timesof that of amido of the chitosan, adding p-Hydroxyanisole accounting for 1-3 percent of the mole number of the 2-acrylamido-2-methylpropanesulfonic acid in the above solution, keeping stirring for 0.5 hour to lead the chitosan to be fully dissolved in the aqueous solution, heating up to 30-60 DEG C fast, and reacting for 2-6 hours, thus obtaining the reactive type water-solubility chitosan derivative. The method has mild reaction condition, easy control, simple procedures, easy control of substitution degree, environment-protecting subsequent treatment and economical reaction process.

Description

technical field [0001] The invention relates to a preparation method of reactive water-soluble chitosan derivatives. Background technique [0002] Chitin is the second largest natural biopolymer in the storage capacity after cellulose in nature. Chitosan is the product of chitin after deacetylation treatment. It is a natural alkaline polysaccharide existing in nature. It is a kind of Environmentally friendly natural polymers widely exist in the shells of shrimps, crabs, insects, maggots, flies and other animals, and are an inexhaustible renewable resource. Chitosan not only has the advantages of non-toxic, harmless, good biocompatibility, biodegradability, etc., but also has many excellent physiological properties such as anticancer, antibacterial, hemostatic, and enhancing human immunity. Therefore, chitosan has great application value in food, cosmetics, environmental protection, textile, printing and dyeing, papermaking and other industries, especially in the fields of b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08
Inventor 马贵平聂俊
Owner BEIJING UNIV OF CHEM TECH
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