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Chitosan aminoethyl quaternary ammonium salt derivative and preparation method thereof

A technology of aminoquaternary ammonium and aminoethyl, which is applied in the field of chitosan aminoethylquaternary ammonium salt derivatives and its preparation, can solve the problems that there are no reports of chitosan aminoethylquaternary ammonium salt derivatives, etc. Achieve good solubility, expand application fields, and improve biological activity

Active Publication Date: 2012-01-18
水母娘娘海洋生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Also do not see the report about chitosan aminoethyl quaternary ammonium salt derivative at present

Method used

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  • Chitosan aminoethyl quaternary ammonium salt derivative and preparation method thereof
  • Chitosan aminoethyl quaternary ammonium salt derivative and preparation method thereof
  • Chitosan aminoethyl quaternary ammonium salt derivative and preparation method thereof

Examples

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Embodiment 1

[0029] The preparation of embodiment 1 derivative 1

[0030] 1.0 grams of aminoethyl chitosan and 3.20 grams of sodium iodide were added to 40 mL of N-methylpyrrolidone, 8 mL of 15% sodium hydroxide was added dropwise to it under stirring, stirred at 60° C. for 20 minutes, 8 mL of methyl iodide was added, and 60 Reaction at ℃ for 60 minutes, precipitation with ethyl ether, washing with ether, dissolving in 50 mL of 10% sodium chloride solution, shaking on a shaker for 18 hours, filtering, dialysis, concentration and freeze-drying to obtain a white cotton-like solid, which is chitosan aminoethyl methyl Base quaternary ammonium salt, that is, derivative 1, see Table 1 for the structural formula.

[0031] Infrared spectrum shows: the infrared spectrum of chitosan derivative 1 ( image 3 ) and the infrared spectrum of aminoethyl chitosan ( figure 2 ) compared to 3030, 2943, 2870cm -1 The hydrocarbon stretching vibration peak of the methyl group is enhanced, and it moves to the...

Embodiment 2

[0034] The preparation of embodiment 2 derivative 2

[0035] Add 3.0 g of aminoethyl chitosan to 120 mL of distilled water, stir to dissolve, add 1.8 mL of n-butyraldehyde dropwise, stir at room temperature for 2 hours, slowly add 38 mL of 10% sodium borohydride dropwise, continue the reaction for 2 hours, and precipitate with acetone after the reaction , the obtained solid was placed and dried at 60° C. to obtain N-substituted aminoethyl chitosan.

[0036] Add 1 gram of N-substituted aminoethyl chitosan and 3.20 grams of sodium iodide to 40 mL of N-methylpyrrolidone, add 8 mL of 15% sodium hydroxide dropwise under stirring, stir at 60°C for 20 minutes, and add 8 mL of iodine Methane, reacted at 60°C for 60 minutes, precipitated with ethanol and ether, washed with ether, dissolved in 50mL of 10% sodium chloride solution, shaken on a shaker for 18 hours, filtered, dialyzed, concentrated and freeze-dried to obtain a white cotton-like solid, which is chitosan ammonia Ethylmethyl...

Embodiment 3

[0038] The preparation of embodiment 3 derivative 3

[0039] Add 3.0 g of aminoethyl chitosan to 120 mL of distilled water, stir and dissolve, then add 1.8 mL of benzaldehyde dropwise, stir at room temperature for 2 hours, slowly add 38 mL of 10% sodium borohydride dropwise, continue the reaction for 2 hours, and precipitate with acetone after the reaction. The obtained solid was placed and dried at 60° C. to obtain N-substituted aminoethyl chitosan.

[0040] Add 1 gram of N-substituted aminoethyl chitosan and 3.20 grams of sodium iodide to 40 mL of N-methylpyrrolidone, add 8 mL of 15% sodium hydroxide dropwise under stirring, stir at 60°C for 20 minutes, and add 8 mL of iodine Methane, reacted at 60°C for 60 minutes, precipitated with ethanol and ether, washed with ether, dissolved in 50mL of 10% sodium chloride solution, shaken on a shaker for 18 hours, filtered, dialyzed, concentrated and freeze-dried to obtain a white cotton-like solid; namely, chitosan ammonia Ethylmethy...

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Abstract

The invention belongs to ocean chemical engineering technology, and specifically relates to a chitosan aminoethyl quaternary ammonium salt derivative and a preparation method thereof. The chitosan aminoethyl quaternary ammonium salt derivative is shown as a formula (I), wherein R1 represents methyl or -H, and R2 represents -CH3, linear alkyl, branched alkyl or -Ar, and n equals to 4-4000. According to the invention, 2-chloroethylamine is subjected to an electrophilic substitution reaction with -NH2 on C2 and -OH on C6 of the chitosan to generate aminoethyl chitosan, amino on which reacts directly with iodomethane to generate N-trimethyl quaternary ammonium salt derivative, or which is subjected to a condensation reaction with aromatic aldehyde or fatty aldehyde to generate Schiff base which is reduced by sodium borohydride and quaternized under effect of iodomethane to obtain chitosan aminoethyl quaternary ammonium salt derivative. According to infrared spectroscopic analysis on the obtained derivative, chitosan and the grafted groups are effectively combined to generate aminoethyl quaternary ammonium salt. According to the invention, aminoethyl quaternary ammonium salt group is introduced into the chitosan structure to increase positive charge level of the chitosan, substantially enhance biological activity of the chitosan, such as antibiosis and sterilization, etc.

Description

technical field [0001] The invention belongs to marine chemical engineering technology, and in particular relates to a chitosan aminoethyl quaternary ammonium salt derivative and a preparation method thereof. Background technique [0002] With the development of society, the market demand for antibacterial drugs, including veterinary drugs and feed additives, pesticides, antibacterial materials, food preservatives, etc. is increasing. Antibiotics are widely used due to their low cost, large output, and good antibacterial effect. However, the abuse of antibiotics leads to the emergence of drug-resistant microorganisms, and causes drug residues to pollute the environment and endanger human health. Therefore, the development of new green antibacterial drugs has become a research hotspot both at home and abroad. [0003] Chitosan (chitosan), also known as chitosan, is the product of chitin deacetylation, and its chemical name is poly(1,4 glycoside)-2-amino-β-D-glucose. It is ...

Claims

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Application Information

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IPC IPC(8): C08B37/08
Inventor 李鹏程孟祥涛邢荣娥于华华刘松秦玉坤李克成崔金会李荣锋李冰
Owner 水母娘娘海洋生物科技有限公司
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