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Preparation method of quaternary ammonium N,O-carboxyetbyl chitosan

A technology of carboxyethyl chitosan and quaternization, which is applied in the field of quaternized N, can solve the problems of insufficient hydrophilic and lipophilic balance, increasing the positive charge of chitosan, and insufficient molecular flexibility. , to achieve the effect of superior flocculation performance, wide application range and improved film-forming performance

Inactive Publication Date: 2007-09-19
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the method of both increasing the positive charge of chitosan and increasing the negative charge of chitosan, and being used to chemically modify chitosan to obtain chitosan derivative products with strong amphoteric characteristics, only Involves the graft quaternization of carboxymethyl chitosan and the carboxymethylation of 2-hydroxypropyltrimethylammonium chloride chitosan, which makes the purpose of improving the charging performance and application performance of chitosan The chitosan derivative product obtained after the method is actually used to chemically modify chitosan is still insufficient in application performance, such as the generated chitosan derivative with strong amphoteric characteristics is very hydrophilic. Good, but there are obvious deficiencies in the balance of hydrophilic and lipophilic properties, and the flexibility of molecules cannot well meet the requirements of practical applications

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0008] (1) 100 grams of chitosan products with a degree of deacetylation of 30% to 100%, use 100 to 1000cm 3 The mass percentage is 10% ~ 50% sodium hydroxide and / or potassium hydroxide aqueous solution, at 200 ~ 2000cm 3 Carry out alkalization at 20~80 DEG C in the isopropanol of 20~80 ℃, the alkalization time is 0.5~24 hours; - Chloropropionic acid is used as a carboxyethylation reagent, and it is carried out under the condition of stirring at 20-90°C for carboxyethylation, and the alkalized material is carboxyethylated for 2-12 hours to obtain carboxyethylation N, O-carboxyethyl chitosan with a substitution degree of 30-300%; 3 The mass percentage is 20-90% glycidyltrialkylammonium chloride and / or 50-1000cm 3 The mass percentage of 20-90% 3-chloro-2-hydroxypropyltrialkylammonium chloride aqueous solution is used as a quaternization reagent, and the quaternization is carried out at 20-95°C in a stirring state, and the alkalized material After quaternization for 2 to 18 ...

Embodiment 2

[0010] (1) 100 grams of deacetylation degree is 100% chitosan product, with 1000cm 3 The mass percentage is 50% potassium hydroxide aqueous solution, at 2000cm 3 Carry out alkalization at 80 DEG C in the isopropanol of the present invention, alkalization time is 24 hours; Carry out carboxyethylation under the condition of condition, the material after alkalization obtains carboxyethylation degree of substitution after 12 hours of carboxyethylation and is 300% N, O-carboxyethyl chitosan; (3) the first The carboxyethylation degree of substitution obtained by the two-step process is 300% N, O-carboxyethylated chitosan material, at 1000cm 3 In the presence of 50% potassium hydroxide aqueous solution, use 1000cm 3 The 3-chloro-2-hydroxypropyltrialkylammonium chloride aqueous solution with a mass percentage of 90% is a quaternization reagent, which is quaternized at 95°C under continuous stirring, and the substitution degree of carboxyethylation is 300% N, O-carboxyethylated chit...

Embodiment 3

[0012] (1) 100 grams of deacetylation degree is 30% chitosan product, with 100cm 3 The mass percentage is 10% sodium hydroxide aqueous solution, at 200cm 3 Carry out alkalization at 20 DEG C in the isopropanol of the present invention, alkalization time is 0.5 hour; Carry out carboxyethylation under the condition of condition, the material after alkalization obtains carboxyethylation degree of substitution after the carboxyethylation of 2 hours and is 30% N, O-carboxyethyl chitosan; (3) the first The carboxyethylation degree of substitution obtained by the two-step process is 30% N, O-carboxyethylated chitosan material, in 100cm 3 In the presence of 10% sodium hydroxide aqueous solution by mass percentage, use 50cm 3 The aqueous solution of glycidyltrialkylammonium chloride with a mass percentage of 20% is a quaternization reagent, which is quaternized at 20°C under continuous stirring, and contains N with a carboxyethylation degree of substitution of 30%. The O-carboxyethy...

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Abstract

The invention provides a method of preparing quaternized N,O-carboxyethyl chitosan with improved water-solubility, charge characteristic, bacteriostatic and antibacterial characteristic, moisture absorption and preservation characteristic, flocculation characteristic, emulsification stability, hydrophilic and oleophilic equilibrium characteristic, metal ion chelated capability, medicament slow release and targeting capability, and fresh-keeping and antisepsis capability. The method includes steps: using 100g chitosan raw material with deacetylation degree of 30-90% as datum quantity, adding alkali metal hydrate water solution and isopropyl alcohol to the raw material, carrying double modifying to the chitosan by quaternizing agent and carboxyethylation agent after alkalizing to obtaining quaternized N,O-carboxyethyl chitosan mixed material, washing the mixed material with alcohol to desalt, pumping and filtrating, separating, dissolving the material to water to obtain uaternized N,O-carboxyethyl chitosan containing water solution, washing the solid material, and drying the material to obtain uaternized N,O-carboxyethyl chitosan product.

Description

1. Technical field [0001] The invention belongs to a preparation method of chitosan derivatives, in particular to a preparation method of quaternized N, O-carboxyethyl chitosan. 2. Background technology [0002] Prior Art: Chitosan, as a natural polysaccharide biopolymer compound whose yield is second only to cellulose, is generally obtained by deacetylation of chitin. Since chitosan has more amino groups than chitin, its application performance has been significantly improved and improved compared with chitin. Chitosan not only maintains the good biodegradability and compatibility of chitin, but also has significantly improved solubility in acidic medium compared with chitin. However, due to the strong hydrogen bond between chitosan molecules, the solubility of chitosan in pure water and alkaline medium is still not very good. This deficiency also affects and limits the further development of chitosan. application. For this deficiency that chitosan exists, people have pr...

Claims

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Application Information

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IPC IPC(8): C08B37/08
Inventor 宋湛谦蔡照胜杨春生商士斌
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY