N-pyridylurea chitosan quaternary ammonium salt and preparation method and application thereof

A technology of pyridyl urea-based shell and quaternary ammonium salt, which is applied in the fields of daily chemicals and medicine, can solve the problems of poor water solubility and affect the range of use of chitosan, and achieve low cost, enhanced water solubility and antioxidant activity, and easy promotion Effect

Active Publication Date: 2017-11-24
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, the application of chitosan and its derivatives in antioxidant properties has attracted people's attention and can be used in the food field. However, due to the poor water solubility of chitosan itse

Method used

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  • N-pyridylurea chitosan quaternary ammonium salt and preparation method and application thereof
  • N-pyridylurea chitosan quaternary ammonium salt and preparation method and application thereof
  • N-pyridylurea chitosan quaternary ammonium salt and preparation method and application thereof

Examples

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Embodiment 1

[0038] (1) Preparation of N-methoxycarbonyl chitosan: Dissolve 1 g of chitosan in 30 mL of distilled water at room temperature, then place it in an ice bath, add 30 mL of methanol when the temperature is lower than 10° C. When the temperature is lower than 5°C, add 2.88mL methyl chloroformate and stir for 6 hours. During this period, the pH value of the solution is controlled by adding triethylamine dropwise to 2-7. After the reaction is completed, precipitate, filter and wash the filter cake with absolute ethanol. Freeze-dry to obtain 1.3 g of the product N-methoxycarbonyl chitosan, which is ready for use.

[0039] (2) N-(2-pyridylureido)-chitosan: get 1gN-methoxycarbonyl chitosan and be dissolved in 20mL mass concentration of 8% lithium chloride in N,N-dimethylacetamide solution , then add 2.58g of 2-aminopyridine, stir and react at 110°C for 12h, precipitate with ethanol directly after the reaction, filter with suction, wash and freeze-dry in vacuum to get N-(2-pyridylureid...

Embodiment 2

[0044](1) Preparation of N-methoxycarbonyl chitosan: Dissolve 1 g of chitosan in 30 mL of distilled water at room temperature, then place it in an ice bath, add 35 mL of methanol when the temperature is lower than 10° C. When the temperature is lower than 5°C, add 3.36mL methyl chloroformate and stir the reaction for 6.5h. During this period, the pH value of the solution is controlled by dropping triethylamine to 2-7. After the reaction is completed, precipitate with absolute ethanol, filter, and wash the filtered The cake was freeze-dried to obtain 1.5 g of the product N-methoxycarbonyl chitosan, which was set aside.

[0045] (2) N-(3-pyridylureido)-chitosan: get 1gN-methoxycarbonyl chitosan and be dissolved in 25mL mass concentration of 8% lithium chloride in N,N-dimethylacetamide solution , then add 3.01g of 3-aminopyridine, stir and react at 110°C for 13h, precipitate with ethanol directly after the reaction, filter with suction, wash and freeze-dry in vacuum to get N-(3-p...

Embodiment 3

[0050] (1) Preparation of N-methoxycarbonyl chitosan: Dissolve 1 g of chitosan in 30 mL of distilled water at room temperature, then place it in an ice bath, add 40 mL of methanol when the temperature is lower than 10° C. When the temperature is lower than 5°C, add 3.84mL methyl chloroformate and stir for 7 hours. During this period, the pH value of the solution is controlled by adding triethylamine dropwise to 2-7. After the reaction is completed, it is precipitated with absolute ethanol and freeze-dried to obtain the product N- Methoxycarbonyl chitosan 1.4g, ready for use.

[0051] (2) N-(4-pyridylureido)-chitosan: get 1g of N-methoxycarbonyl chitosan and be dissolved in 30mL of N,N-dimethylacetamide whose mass concentration is 8% lithium chloride solution, and then add 3.44g of 4-aminopyridine, stirred and reacted at 110°C for 14h, precipitated with ethanol directly after the reaction, and obtained N-(4-pyridylureido) after suction filtration, washing, and vacuum freeze-dry...

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Abstract

The invention discloses N-pyridylurea chitosan quaternary ammonium salt and a preparation method and an application thereof. The N-pyridylurea chitosan quaternary ammonium salt takes chitosan, methyl chloroformate, aminopyridine and iodomethane as raw materials, the preparation method comprises the following steps: preparing N-methoxycarbonyl chitosan, reacting N-methoxycarbonyl chitosan and aminopyridine, reacting the obtained N-pyridylurea chitosan and iodomethane, and purifying the product to obtain the N-pyridylurea chitosan quaternary ammonium salt. The prepared N-pyridylurea chitosan quaternary ammonium salt can be used for preparing an anti-oxidant, and can be widely used in the fields of biology, medicine, food and chemical industry, the biological activity such as antioxidant activity is increased, the preparation raw materials are easily available, the preparation is simple, the condition is mild, and the preparation method establishes a base for application and exploitation for high-value chitosan.

Description

technical field [0001] The invention relates to the fields of daily chemicals and medicines, in particular to an N-pyridylureidyl chitosan quaternary ammonium salt and a preparation method and application thereof. Background technique [0002] Chitosan, also known as deacetylated chitin, is obtained by deacetylation of chitin that exists widely in nature. The chemical name is polyglucosamine. Chitosan has high reactivity due to its special molecular structure and polycationic properties. Activity and chemical modifiability can generate various chitosan derivatives with different properties, thus expanding the application range of chitosan. In recent years, the application of chitosan and its derivatives in antioxidant properties has attracted people's attention and can be used in the food field. However, due to the poor water solubility of chitosan itself, the scope of use of chitosan has been seriously affected. , Through the chemical modification of chitosan, derivatives ...

Claims

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Application Information

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IPC IPC(8): C08B37/08C09K15/22
CPCC08B37/003C09K15/22
Inventor 郭占勇张晶晶谭文强栾芳魏丽杰宓英其董方李青
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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