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O-fumarate ester-N-chitosan quaternary ammonium salt and preparation method and application thereof

A technology of chitosan quaternary ammonium salt and fumarate, which is applied in the field of functional derivative O-fumarate-N-chitosan quaternary ammonium salt and its preparation, can solve the problems of limiting antibacterial applications and achieve enhanced antibacterial Activity and hydrophilicity, good antibacterial properties, and the effect of expanding the range of applications

Inactive Publication Date: 2014-07-30
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Chitosan macromolecules are insoluble in water, which limits their antibacterial applications

Method used

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  • O-fumarate ester-N-chitosan quaternary ammonium salt and preparation method and application thereof
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  • O-fumarate ester-N-chitosan quaternary ammonium salt and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] A kind of O-fumarate-N-chitosan quaternary ammonium salt, its preparation method is as follows:

[0033] (1) Add 3g of a viscosity-average molecular weight of 5.0×10 to a three-necked flask 4 , chitosan with a deacetylation degree of 95%, add 50mL of isopropanol, stir and make it swell for 0.5h, then add 25mL of 40wt% sodium hydroxide solution, stir for 6h to make chitosan alkaline at 25°C Form a swellable alkalization center under the conditions, then add 9g of 2,3-epoxypropyltrimethylammonium chloride in several times, transfer to a microwave reaction instrument and microwave for 120min under the condition of 40°C and 600W , washed and filtered with 95% (v / v) ethanol solution, added acetone for precipitation, and dried under vacuum at 60° C. to obtain N-chitosan quaternary ammonium salt.

[0034] The degree of substitution of N-chitosan quaternary ammonium salt was measured to be 61.4% by potentiometric titration.

[0035] (2) Take 1.16g of fumaric acid and disperse...

Embodiment 2

[0038] A kind of O-fumarate-N-chitosan quaternary ammonium salt, its preparation method is as follows:

[0039] (1) Add 3g of a viscosity-average molecular weight of 5.0×10 to a three-necked flask 4 , chitosan with a deacetylation degree of 95%, add 50mL of isopropanol, stir and make it swell for 0.5h, then add 25mL of 40wt% sodium hydroxide solution, stir for 6h to make chitosan alkaline at 25°C Form a swollen alkalization center under the conditions, then add 15g of 2,3-epoxypropyltrimethylammonium chloride several times, transfer to a microwave reaction instrument, and microwave for 90min under the condition of 50°C and 600W , washed and filtered with 95% (v / v) ethanol solution, added acetone for precipitation, and dried under vacuum at 60° C. to obtain N-chitosan quaternary ammonium salt.

[0040] The degree of substitution of the N-chitosan quaternary ammonium salt was measured to be 69% by potentiometric titration.

[0041] (2) Disperse 2.32g of fumaric acid in 10mL of...

Embodiment 3

[0044] A kind of O-fumarate-N-chitosan quaternary ammonium salt, its preparation method is as follows:

[0045] (1) Add 3g of a viscosity-average molecular weight of 5.0×10 to a three-necked flask 4 , chitosan with a deacetylation degree of 95%, add 50mL of isopropanol, stir and make it swell for 0.5h, then add 25mL of 40wt% sodium hydroxide solution, stir for 6h to make chitosan alkaline at 25°C Form a swellable alkalization center under the conditions, then add 21g of 2,3-epoxypropyltrimethylammonium chloride in several times, transfer to a microwave reaction instrument and microwave for 60min at 70°C and 700W , washed and filtered with 95% (v / v) ethanol solution, added acetone for precipitation, and dried under vacuum at 60° C. to obtain N-chitosan quaternary ammonium salt.

[0046] The degree of substitution of the N-chitosan quaternary ammonium salt was measured to be 78% by potentiometric titration.

[0047] (2) Take 3.48g of fumaric acid and disperse it in 10mL of dic...

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Abstract

The invention belongs to the field of a macromolecule compound material and discloses a chitosan chemically-modified functional derivative O-fumarate ester-N-chitosan quaternary ammonium salt and a preparation method and application thereof. The preparation method of the O-fumarate ester-N-chitosan quaternary ammonium salt comprises the following steps: carrying out microwave reaction between chitosan and 2,3-epoxypropyl trimethyl ammonium chloride to prepare an N-chitosan quaternary ammonium salt; reacting fumaryl chloride prepared from a fumaric acid and thionyl chloride with N-chitosan quaternary ammonium salt to prepare the O-fumarate ester-N-chitosan quaternary ammonium salt. The O-fumarate ester-N-chitosan quaternary ammonium salt not only has good water solubility, and is greatly improved in term of the antibacterial property as compared with the chitosan; the O-fumarate ester-N-chitosan quaternary ammonium salt can be applied to a plurality of application fields such as antibacterial materials, daily chemical products, industrial wastewater and the like.

Description

technical field [0001] The invention belongs to the field of polymer compound materials, and in particular relates to a chitosan chemically modified functional derivative O-fumarate-N-chitosan quaternary ammonium salt and a preparation method and application thereof. Background technique [0002] With the development of society and the advancement of science and technology, people pay more and more attention to antibacterial materials. There are three main types of antibacterial agents commonly used in daily life: inorganic metal mineral materials, organic heterocyclic antibacterial materials and natural antibacterial materials. Because natural antibacterial preservatives come from nature, are highly safe to the human body, and meet the requirements of green environmental protection, they have been welcomed by people in recent years. The research, development and utilization of natural antibacterial agents have become a hot spot in applied chemistry. [0003] Chitosan is wi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08
Inventor 杨仁党李知函程峥
Owner SOUTH CHINA UNIV OF TECH
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