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Preparation method of antibacterial chitosan quaternary ammonium salt and product

A technology of quaternary ammonium salt and antibacterial shell, which is applied in the field of preparation of antibacterial chitosan quaternary ammonium salt, can solve the problems of cytotoxic hemolysis and poor biocompatibility, and achieve good biocompatibility, low biocompatibility, The effect of improving the antibacterial effect

Active Publication Date: 2019-09-17
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the biocompatibility of long alkyl chain epoxy quaternary ammonium salt alone is poor, and it will cause severe cytotoxicity and hemolysis, so it cannot be used in the field of contact with human tissue, and its application has certain limitations.

Method used

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  • Preparation method of antibacterial chitosan quaternary ammonium salt and product
  • Preparation method of antibacterial chitosan quaternary ammonium salt and product
  • Preparation method of antibacterial chitosan quaternary ammonium salt and product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthetic antibacterial chitosan quaternary ammonium salt X1, comprises the following steps::

[0026] 1) Add 3g of epichlorohydrin dropwise to 4g of N,N-dimethylhexylamine, stir at 55°C for 2h, after the end, precipitate and wash with petroleum ether twice, and dry under reduced pressure to obtain long-chain alkyl chain epoxy Quaternary ammonium salt A1 (2-Oxiranemethanaminium, N-hexane-N, N-dimethyl-), the molecular formula is

[0027] 2) Add 1.0g of epichlorohydrin dropwise to 1.0g of N,N-dimethylethylamine, stir at 50°C for 36 hours, after the end, precipitate and wash with ether twice, dry under reduced pressure to obtain short-chain alkyl Epoxy quaternary ammonium salt B1, the molecular formula is

[0028] 3) Add 10g of chitosan hydrochloride (deacetylation degree 85%, molecular weight 80,000) into 2L of water, heat and dissolve at 60°C, add hydrochloric acid to adjust pH=4, and then mix 15g of epoxy quaternary ammonium salt A1 and 7.5 g epoxy quaternary amm...

Embodiment 2

[0031] Synthesis of antibacterial chitosan quaternary ammonium salt X2, comprising the following steps:

[0032] 1) Add 2g of epichlorohydrin dropwise to 4g of N,N-dimethyloctylamine, stir at 40°C for 24h, after the end, precipitate and wash with ether twice, dry under reduced pressure to obtain long alkyl chain epoxy quaternary ammonium salt A2 (2-Oxiranemethanaminium, N-octyl-N, N-dimethyl-), the molecular formula is

[0033] 2) Add 2.0g of epichlorohydrin dropwise to 5.0g of N,N-dimethylpropylamine, stir at 40°C for 6 hours, after the end, precipitate and wash with ether twice, dry under reduced pressure to obtain epoxy quaternary ammonium salt B2, Molecular formula is

[0034] 3) Add 5 g of chitosan citrate (deacetylation degree 85%, molecular weight 80,000) into 500 mL water, heat and dissolve at 70° C., adjust pH=5 with citric acid. Afterwards, 7.5 g of epoxy quaternary ammonium salt A2 and 3 g of epoxy quaternary ammonium salt B2 were dissolved in 20 mL of deioniz...

Embodiment 3

[0037] Synthetic antibacterial chitosan quaternary ammonium salt X3, comprises the following steps:

[0038] 1) Add 3g of epichlorohydrin dropwise to 5g of N,N-dimethyldecylamine, heat and stir at 50°C for 3h, after the reaction is completed, wash the reaction solution with n-hexane precipitation three times, and then vacuum dry to obtain quaternization Reagent A3 (2-Oxiranemethanaminium, N-decyl-N, N-dimethyl-), the molecular formula is:

[0039]

[0040] 2) Add 1.0g of epichlorohydrin dropwise to 4.0g of N,N-dimethylbutylamine, stir at 40°C for 4 hours, after the end, precipitate and wash with ether twice, dry under reduced pressure to obtain epoxy quaternary ammonium salt B3, the molecular formula is

[0041] 3) Add 5 g of chitosan hydrochloride (deacetylation degree 90%, molecular weight 30,000) into 500 mL deionized water, heat to dissolve at 50° C., and adjust pH=3. After that, 4g of epoxy quaternary ammonium salt A3 and 2g of epoxy quaternary ammonium salt B3 wer...

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Abstract

The invention provides a preparation method of an antibacterial chitosan quaternary ammonium salt. The preparation method comprises the following steps: 1) preparing a chitosan solution; 2) adding a long alkyl chain epoxy quaternary ammonium salt and a short alkyl chain quaternary ammonium salt, and carrying out a reaction; and 3) settling the reaction liquid of the step 2), and carrying out washing and drying, so as to obtain a product. As the long alkyl chain epoxy quaternary ammonium salt and the short alkyl chain quaternary ammonium salt are cografted on chitosan, antibacterial chitosan has intensive electropositivity, and can be well combined with a bacterial membrane with negative electricity, and thus an antibacterial effect can be improved. The cografting ratio of the two components is optimized and adjusted, so that the biocompatibility of the antibacterial chitosan can be effectively improved while an antibacterial effect is ensured

Description

technical field [0001] The invention belongs to the field of antibacterial materials, and relates to a preparation method and product of antibacterial chitosan quaternary ammonium salt. Background technique [0002] Chitosan is the product of deacetylation of chitin. Because of its renewability, good biocompatibility and many unique physiological and pharmacological functions, it is widely used in medicine, food, daily chemical, textile, agriculture and other fields. Its application and development prospects are broad. The Chinese invention patent publication with the publication number CN101929074A discloses a preparation method of chitosan quaternary ammonium salt, which is characterized in that a C4-18 alkyl dimethyl tertiary amine is used to react with epichlorohydrin to obtain a chitosan quaternary ammonium salt. Long alkyl chain epoxy quaternary ammonium salt, and then use long alkyl chain epoxy quaternary ammonium salt to undergo epoxy ring-opening reaction with chit...

Claims

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Application Information

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IPC IPC(8): C08B37/08
CPCC08B37/003
Inventor 徐福建胡杨王俊尧
Owner BEIJING UNIV OF CHEM TECH
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