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Chitosan-hydrocarbyl urea and preparation method thereof

A technology of chitosan and hydrocarbyl urea, which is applied in the field of natural polymers and their chemical modification, to achieve the effect of high degree of substitution and regular structure

Inactive Publication Date: 2017-08-25
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the ureidation of chitosan
[0006] In addition, there is currently no mature method that can effectively urea-sylate the amino group in the chitosan molecule under the condition that the hydroxyl group is not reacted.

Method used

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  • Chitosan-hydrocarbyl urea and preparation method thereof
  • Chitosan-hydrocarbyl urea and preparation method thereof
  • Chitosan-hydrocarbyl urea and preparation method thereof

Examples

Experimental program
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preparation example Construction

[0031] The preparation method of chitosan used in the present invention and the measuring method of molecular weight all refer to literature [(6) Bai Zhengwu etc., chitosan-two (aryl carbamate)-(amide) and preparation method thereof [P ], application number: 201410594564.2].

[0032] The used N,N-dimethylacetamide (DMAc) of the present invention passes through before using Molecular sieves were dried three times, and LiCl was vacuum-dried at 140°C for more than 24 hours or calcined at 300°C for more than 3 hours before use.

Embodiment 1

[0034] Synthesis of Chitosan-Benzylurea:

[0035]The synthesis of chitosan-N-methoxy formamide: 1.0g (6.2mmol repeating unit) chitosan (number average molecular weight 90,000, deacetylation degree is 99.2%) is joined in the 250mL there-necked bottle, add dilute hydrochloric acid Stir to dissolve chitosan until clear and transparent. Then add 35g of methanol under the ice-water bath, stir evenly, then quickly add 5.9g of methyl chloroformate (62.7mmol), control the temperature at 2-10°C for 8h, add triethylamine during the reaction to adjust the pH value of the system, and control the pH The value is between 2-7. After the reaction is complete, add 50 mL of ethanol to the reaction flask and stir vigorously, filter, wash the product with ethanol until neutral, and dry to obtain 1.27 g of chitosan-N-methoxyformamide, yield: 93%; infrared The spectrogram is attached figure 1 (a) Shown: IR(KBr,cm -1 )υ:3439,3325(-OH,-NH-),2950-2887(-C-H),1704(-COOCH 3 ), 1549 (-NH-).

[0036]...

Embodiment 2

[0038] Synthesis of chitosan-n-butylurea:

[0039] Preparation of chitosan-N-methoxy formamide: add 1.0g (6.2mmol repeating unit) chitosan (number average molecular weight 30,000, degree of deacetylation 99.7%) to a 250mL three-necked flask, add dilute hydrochloric acid and stir Dissolve chitosan until clear and transparent. Then add 28g of methanol under the ice-water bath, stir evenly, quickly add 4.82g of methyl chloroformate (51.3mmol), control the temperature at 2-8°C for 8h, add triethylamine during the reaction to adjust the pH value of the system, and control the pH The value is between 2-7. After the reaction was completed, 50 mL of ethanol was added into the reaction flask and stirred vigorously, filtered, the product was washed with ethanol until neutral, and dried to obtain 1.25 g of chitosan-N-methoxyformamide, yield: 92%.

[0040] Preparation of chitosan-n-butylurea: Take 1.2g of dry LiCl in a 50mL three-necked flask, add 15mL of dry DMAc, heat to completely di...

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Abstract

The invention relates to a chitosan-alkyl urea and a preparation method thereof. The preparation method comprises the following steps: 1) dissolving chitosan with the deacetylation degree of 98% or above in dilute hydrochloric acid, adding methanol and methylchloroformate into the obtained solution, adding triethylamine at low temperature to control the pH value of the reaction system, and stirring to obtain chitosan-N-methoxy formamide; and 2) dissolving the chitosan-N-methoxy formamide obtained in the step 1) in a lithium chloride N,N-dimethylacetamide solution, adding amine, and reacting for 6-24 hours to obtain the chitosan-alkyl urea. The prepared uramido chitosan has the advantages of high substitution degree and regular structure, can satisfy multiple application demands, and can adopt the chitosan with the deacetylation degree of 98% or above instead of the completely deacetylated chitosan; and the method can obtain chitosan derivatives with more diversified structures.

Description

technical field [0001] The invention relates to a natural polymer and a chemical modification method thereof, in particular to chitosan-hydrocarbyl urea and a preparation method thereof. Background technique [0002] Chitosan, whose chemical name is poly(1,4 glycoside)-2-amino-β-D-glucose, is a natural aminopolysaccharide existing in nature. Due to its unique physiological and pharmacological functions and good biological Compatibility and antibacterial properties, non-toxic, harmless, and easy to biodegrade, it is widely used in various fields such as medicine, food, cosmetics, agriculture, chemical industry, environmental protection, gene delivery, cell culture, and tissue engineering. In order to further expand the application range of chitosan, it is of great significance to chemically modify its amino and hydroxyl groups to develop new products, especially to selectively modify its amino groups. [0003] Okamoto et al[(1) Zhang L., Shen J., Zuo W., Okamoto Y., Synthesi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08
Inventor 柏正武王靖陈伟
Owner WUHAN INSTITUTE OF TECHNOLOGY
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