Chitosan alpha-aminoalkyl phosphonate ester derivative and preparation method thereof

A technology of aminoalkylphosphonic acid and chitosan, which is applied in the field of marine chemical engineering, can solve problems such as poor effect, achieve good water solubility, overcome poor solubility, and have wide application value

Inactive Publication Date: 2008-04-09
INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, it has been reported that chitosan is used in veterinary drugs and pesticides as a bacteriostatic agent, but the results are not good.

Method used

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  • Chitosan alpha-aminoalkyl phosphonate ester derivative and preparation method thereof
  • Chitosan alpha-aminoalkyl phosphonate ester derivative and preparation method thereof
  • Chitosan alpha-aminoalkyl phosphonate ester derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Dissolve 1.35g of chitosan propionaldehyde Schiff base with a molecular weight of 80,000 in 40mL of benzene, add 10mL of dimethyl phosphite under stirring, and react at 80°C for 6 hours. Concentrate under reduced pressure to 30 mL and cool to room temperature. Pour the reaction mixture into 300 mL of absolute ethanol to obtain a precipitate. After standing for 8 hours, filter and wash the precipitate with absolute ethanol, add 100 mL of distilled water to dissolve, and put it into a dialysis bag with a molecular weight cut-off of 3600. , dialyzed in distilled water for 2-3 days, concentrated to 31ml ± 1ml by rotary evaporation, and freeze-dried to obtain chitosan α-aminopropyl phosphonic acid dimethyl derivatives. Structural formula see formula 1, wherein R=-CH 3 , R 1 for -CH 2 CH 3 , n=49.

[0043] Infrared spectrum analysis showed that chitosan α-aminopropylphosphonic acid dimethyl ester derivatives (see Figure 2) compared with chitosan (see Figure 1): at 3447.01...

Embodiment 2

[0045] Dissolve 1.51g of chitosan propionaldehyde Schiff base with a molecular weight of 500,000 in 60mL of benzene, add 10mL of dimethyl phosphite under stirring, and react at 90°C for 7 hours. Concentrate under reduced pressure to 40 mL and cool to room temperature. Pour the reaction mixture into 300 mL of absolute ethanol to obtain a precipitate. After standing for 8 hours, filter and wash the precipitate with absolute ethanol, add 100 mL of distilled water to dissolve, and put it into a dialysis bag with a molecular weight cut-off of 3300. , dialyzed in distilled water for 2-3 days, concentrated to 35ml ± 1ml by rotary evaporation, and freeze-dried to obtain chitosan α-aminopropylphosphonic acid dimethyl ester derivatives. Structural formula see formula 1, wherein R=-CH 3 , R 1 for -CH 2 CH 3 , n=3106.

[0046] Infrared spectrum analysis shows that chitosan α-aminopropyl phosphonic acid dimethyl ester derivative (see Figure 3) is compared with chitosan (see Figure 1): ...

Embodiment 3

[0048] Dissolve 1.79g of chitosan propionaldehyde Schiff base with a molecular weight of 20,000 in 40mL of benzene, add 10mL of diethyl phosphite under stirring, and react at 90°C for 6 hours. Concentrate under reduced pressure to 35 mL and cool to room temperature. Pour the reaction mixture into 300 mL of absolute ethanol to obtain a precipitate. After standing for 8 hours, filter and wash the precipitate with absolute ethanol, add 100 mL of distilled water to dissolve, and put it into a dialysis bag with a molecular weight cut-off of 3400. , dialyzed in distilled water for 2-3 days, concentrated to 39ml ± 1ml by rotary evaporation, and freeze-dried to obtain chitosan α-aminopropylphosphonic acid diethyl ester derivatives. Structural formula see formula 1, wherein R=-CH 2 CH 3 , R 1 for -CH 2 CH 3 , n=124.

[0049] Infrared spectrum analysis shows that chitosan α-aminopropyl phosphonic acid diethyl ester derivative (see Figure 4) is compared with chitosan (see Figure 1):...

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Abstract

The present invention relates to the technical field of marine chemical engineering, in particular to a chitosan Alpha-amino alkyl phosphonate ester derivative and a preparation method thereof. The derivative is a compound with a formula (1) specifically, the preparation method is that: the chitosan firstly reacts with aldehyde to prepare the schiff base of the chitosan; then the schiff base of the chitosan reacts with phosphate ester to prepare the chitosan Alpha-amino alkyl phosphonate ester derivative. The degree of substitution of the chitosan alpha-amino alkyl phosphonate ester derivative which is synthesized by the preparation method of the present invention can achieve 21.03 to 58.65 percent and have better water solubility, the Alpha-amino alkyl phosphonate ester groups can be effectively combined with the chitosan molecules, which can generate the synergy and significantly enhance the specific biological activities of antibacterial, anti-virus and so on of the chitosan, so the present invention can be applied in the medicine, agriculture and other fields.

Description

technical field [0001] The invention relates to the technical field of marine chemical engineering, in particular to a chitosan alpha-aminoalkylphosphonate derivative and a preparation method thereof. Background technique [0002] With the improvement of living standards and the development of pollution-free food, people pay more and more attention to the residues of harmful substances such as antibiotics and pesticides in livestock and poultry products, fruits and vegetables. In view of the above, safe, efficient, low-toxic and green products have become the research and development trend of new veterinary drugs and pesticides in the 21st century. In order to meet this requirement, the development and research of natural products with antibacterial activity has become a research hotspot. At present, some people use pure natural products as antibacterial agents, but the effect is not good. Simply modifying natural products to obtain new derivatives, and conducting in-depth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08
Inventor 李鹏程钟志梅邢荣娥刘松王琳蔡圣宝
Owner INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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