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Chitosan thiosemicarbazone derivatives and preparation method thereof

A technology of thiosemicarbazone and derivatives, which is applied in the field of chitosan thiosemicarbazone derivatives and the preparation thereof, can solve problems such as poor effect, achieve good water solubility, overcome poor solubility, and be easily absorbed. Effect

Inactive Publication Date: 2009-07-08
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 thiosemicarbazone derivatives and preparation method thereof
  • Chitosan thiosemicarbazone derivatives and preparation method thereof
  • Chitosan thiosemicarbazone derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 0.612g of acetylated chitosan with a molecular weight of 08,000 was dissolved in 80ml of 2% HAc, and 1.19g of thioanisemicarbazide was added under stirring, and reacted at 100°C for 8 hours. Concentrate under reduced pressure and cool to room temperature. Pour the reaction mixture into 300ml of absolute ethanol to obtain a precipitate. After standing for 8 hours, filter and wash the precipitate with absolute ethanol, dry at 50°C to obtain a brown powder, and use absolute ethanol as a solvent for Soxhlet extraction. After drying for 1 hour, the thiosemicarbazone derivative of acetylated chitosan is obtained. The structural formula is shown in formula 1, wherein R=-CH 3 , R 1 for n=49.

[0030] For the preparation of the acetylated chitosan, refer to Huang Liyao, Liu Chao, Preparation of Hydrophobic Long Fatty Chain Acylated Chitosan, Journal of Huaqiao University, 439-441.

[0031] Infrared spectroscopy analysis shows that the acetylthiosemicarbazone derivatives of c...

Embodiment 2

[0033] 0.90 g of acetylated chitosan with a molecular weight of 200,000 was dissolved in 80 ml of 2% HAc, and 1.0 g of thioanisemicarbazide was added under stirring, and reacted at 100° C. for 10 hours. Concentrate under reduced pressure and cool to room temperature, pour the reaction mixture into 300ml of absolute ethanol to obtain a precipitate, filter and wash the precipitate with absolute ethanol, dry at 55°C to obtain a brown powder, use absolute ethanol as a solvent for Soxhlet extraction for 10 hours, and dry Obtain the thiosemicarbazone derivative of acetylated chitosan, the structural formula is referring to formula 1, wherein R=-CH 3 , R 1 for n=1240.

[0034] Infrared spectroscopy analysis shows that the acetylthiosemicarbazone derivatives of chitosan (see image 3 ) and acetylated chitosan (see figure 1 ) compared to: at 3207 and 3112cm -1 The sharper absorption peak at v NH The characteristic absorption peak of 1653.82cm -1 It is the characteristic absorpt...

Embodiment 3

[0036] 0.738g of acetylated chitosan with a molecular weight of 20,000 was dissolved in 60ml of 2% HAc, and 1.086g of p-toluenethiosemicarbazide was added under stirring, and reacted at 100°C for 9 hours. Concentrate under reduced pressure and cool to room temperature. Pour the reaction mixture into 300ml of acetone to obtain a precipitate. After filtering, wash the precipitate with acetone and dry at 50°C to obtain a brown powder. Soxhlet extract with absolute ethanol for 8 hours and then dry to obtain the acetylated shell. p-toluidine thiosemicarbazone derivatives of polysaccharides, the structural formula is shown in formula 1, wherein R=-CH 3 , R 1 for n=124.

[0037] Infrared spectroscopy analysis shows that the acetyl p-toluidine thiosemicarbazone derivatives of chitosan (see Figure 4 ) and acetylated chitosan (see figure 1 ) compared to: at 3193 and 3120cm -1 The sharper absorption peak at v NH The characteristic absorption peak, 1660cm -1 It is the characteris...

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Abstract

The invention relates to the technical field of marine chemical engineering, in particular to a novel chitosan thiosemicarbazide derivative and a preparation method thereof. The specific derivative is the compound of formula (1): wherein n=49-1242; R is -CH3 or -Ar; R1 is the formula below right. The preparation method is as follows: reacting acylated chitosan with different substituent anilinothiourea in HAc solvent; then using an organic solvent to precipitate the reaction product, filtering and washing the precipitate with the organic solvent, and drying the washed precipitate Soxhlet extraction with organic solvent, the extract is the derivative after vacuum drying. The substitution degree of the derivatives prepared by the invention reaches 18.2-35.6%, the water solubility is good, and the thiosemicarbazone groups are effectively combined with the chitosan molecules, which can produce a synergistic effect and significantly enhance the unique properties of chitosan itself. Antibacterial, antiviral and other biological activities can be used in medicine, cosmetics, agriculture and other fields.

Description

technical field [0001] The invention relates to the technical field of marine chemical engineering, in particular to a chitosan thiosemicarbazone 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 addition, most of the heavy metal ions such as lead, arsenic and mercury are used in cosmetics. As a bacteriostatic agent, these metal ions will gradually accumulate and remain in the human body to produce toxic and side effects. In view of the above, safe, efficient, low-toxic and green products have become the research and development trend of new veterinary drugs, pesticides and cosmetics in the 21st century. In order to meet this requirement, the development and research of natural products with antibact...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08C08K5/405
Inventor 李鹏程钟志梅邢荣娥刘松王琳
Owner INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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