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N-thiosemicarbazide-O-quaternary ammonium chitosan oligosaccharide and preparation method and application thereof

A technology of thiosemicarbazide and salt chitosan oligosaccharide is applied in the preparation of sugar derivatives, botanical equipment and methods, applications, etc., and can solve the problems of inability to use for a long time, easy to be dissolved and corroded, poor adsorption performance of chitosan oligosaccharide, etc. To achieve the effect of improving bacteriostatic performance, good metal adsorption and complexing ability and bacteriostatic ability, and high reaction efficiency

Active Publication Date: 2017-11-03
南通药享科技有限公司
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  • Description
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Problems solved by technology

[0005] From the performance of the modification of chitosan oligosaccharide in the adsorption and bactericidal properties of the prior art, the inventors of the present application have found that it has the following problems: the chitosan oligosaccharide has poor adsorption performance, is easily dissolved and corroded, and cannot be used in acidic or alkaline aqueous solutions. long-term use

Method used

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  • N-thiosemicarbazide-O-quaternary ammonium chitosan oligosaccharide and preparation method and application thereof
  • N-thiosemicarbazide-O-quaternary ammonium chitosan oligosaccharide and preparation method and application thereof
  • N-thiosemicarbazide-O-quaternary ammonium chitosan oligosaccharide and preparation method and application thereof

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preparation example Construction

[0029] (1) Preparation of N-methylene chitosan oligosaccharides: Chitosan oligosaccharides are prepared into chitosan oligosaccharide aqueous solution, formaldehyde solution is added dropwise to the chitosan oligosaccharide aqueous solution, after the addition is completed, stir at room temperature for a period of time to obtain N- Methylene chitooligosaccharides;

[0030] (2) Preparation of N-methylene-O-quaternary ammonium chitosan oligosaccharide: the N-methylene chitosan oligosaccharide prepared in step (1) is added to an organic solvent for swelling, and then the aqueous solution of alkali is added to continue swelling, After heating, add 3-chloro-2-hydroxypropyltrimethylammonium chloride, and stir to get N-methylene-O-quaternary ammonium chitosan oligosaccharide;

[0031] (3) Synthesis of N-thiosemicarbazide-O-quaternary ammonium chitosan oligosaccharide: the N-methylene-O-quaternary ammonium chitosan oligosaccharide prepared in step (2) was added to water to make modifi...

Embodiment 1

[0053] (1) Preparation of N-methylene chitooligosaccharides

[0054] Dissolve 4 g of chitosan oligosaccharide in 50 mL of deionized water, take 9.3 mL of formaldehyde solution with a concentration of 15%, add it dropwise to the above solution, and stir for 4 h. 4 times the volume of ethanol was settled, filtered with suction, washed twice with ethanol, and vacuum-dried at 40°C until constant weight.

[0055] (2) Preparation of N-methylene O-quaternary ammonium chitosan oligosaccharide

[0056] Weigh 2g of the dried product in (1) and fully swell in 30mL of isopropanol, add 10mL of 40% NaOH solution, after continuing to swell, add 1.32g of 3-chloro-2-hydroxypropyltrimethyl chloride at 80°C Ammonium chloride was stirred for 24h. Adjust the pH to neutral, settle with 4 times the volume of acetone, filter with suction, wash with 80wt.%, 90wt.% and absolute ethanol in turn, and dry in vacuum at 40°C until constant weight.

[0057] (3) Synthesis of N-thiosemicarbazide-O-quaternar...

Embodiment 2

[0060] (1) Preparation of N-methylene chitooligosaccharides

[0061] Dissolve 4 g of chitosan oligosaccharide in 50 mL of deionized water, take 9.5 mL of formaldehyde solution with a concentration of 15%, add it dropwise to the above solution, and stir for 4 h. 4 times the volume of ethanol was settled, filtered with suction, washed twice with ethanol, and vacuum-dried at 40°C until constant weight.

[0062] (2) Preparation of N-methylene-O-quaternary ammonium chitosan oligosaccharide

[0063] Weigh 2g of the dried product in (1) and fully swell in 30mL of isopropanol, add 10mL of 40% NaOH solution, after continuing to swell, add 1.32g of 3-chloro-2-hydroxypropyltrimethyl chloride at 80°C Ammonium chloride was stirred for 24h. Adjust the pH to neutral, settle with 4 times the volume of acetone, filter with suction, wash with 80wt.%, 90wt.% and absolute ethanol in turn, and dry in vacuum at 40°C until constant weight.

[0064] (3) Synthesis of N-thiosemicarbazide-O-quaternar...

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Abstract

The invention discloses N-thiosemicarbazide-O-quaternary ammonium chitosan oligosaccharide and a preparation method and an application of the N-thiosemicarbazide-O-quaternary ammonium chitosan oligosaccharide and preparation method and application. The structural formula of the N-thiosemicarbazide-O-quaternary ammonium chitosan oligosaccharide is shown in the description. The preparation method comprises the following steps: enabling formaldehyde and an amino on the chitosan oligosaccharide to react to obtain N-methylene chitosan oligosaccharide, enabling 3-chlorine-2-hydroxypropyl trimethyl ammonium chloride and a hydroxyl on C6 site of the N-methylene chitosan oligosaccharide to react to obtain N-methylene-O-quaternary ammonium chitosan oligosaccharide, finally enabling thiosemicarbazide and a carbon-nitrogen double bond of the N-methylene-O-quaternary ammonium chitosan oligosaccharide to have an addition reaction to obtain the N-thiosemicarbazide-O-quaternary ammonium chitosan oligosaccharide. The N-thiosemicarbazide-O-quaternary ammonium chitosan oligosaccharide solves the problems that chitosan oligosaccharide and chitosan derivatives are poor in adsorbability and are easy to dissolve and corrode, and can be used in acid, neutral and alkaline solutions. Moreover, the antibacterial activity of the N-thiosemicarbazide-O-quaternary ammonium chitosan oligosaccharide is improved, and the N-thiosemicarbazide-O-quaternary ammonium chitosan oligosaccharide has excellent effects on adsorbing metal ions and inhibiting bacteria.

Description

technical field [0001] The invention relates to an N-thiosemicarbazide-O-quaternary ammonium chitosan oligosaccharide, a preparation method and application thereof. Background technique [0002] The rapid development of modern industry has caused increasingly serious pollution of water resources, and even affected the safety of groundwater. Similarly, a large number of corrosion phenomena and microbial contamination seriously affect the safety of industrial facilities, public health facilities and daily facilities. The use of some materials, such as metal corrosion inhibitors, metal ion adsorbents and bacteriostats, mostly relies on chemically synthesized materials. The inefficiency and high energy consumption of traditional materials, the pollution caused by the chemical synthesis process, and the new pollution caused by the use of materials make it imperative to develop and use green and environmentally friendly natural source products for water treatment agents, preserva...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08C07H15/12C07H1/00C02F1/28A01N47/34A01P1/00C02F101/20
CPCA01N47/34C02F1/286C02F2101/20C02F2303/04C07H1/00C07H15/12C08B37/003
Inventor 侯昭升尹胜男
Owner 南通药享科技有限公司
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