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Carbamide-containing acetylated chitosan quaternary ammonium salt, and preparation method and application thereof

A technology of acetylated chitosan and chitosan, which is applied in the field of daily chemicals, can solve the problems of poor water solubility and affecting the range of use of chitosan, and achieve the effects of improved biological activity, easy availability of equipment and raw materials, and easy promotion

Active Publication Date: 2017-09-29
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the poor water solubility of chitosan itself, the scope of use of chitosan has been seriously affected. Through chemical modification of chitosan, derivatives with better water solubility can be obtained, which is very important for the application of high-value chitosan development is important

Method used

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  • Carbamide-containing acetylated chitosan quaternary ammonium salt, and preparation method and application thereof
  • Carbamide-containing acetylated chitosan quaternary ammonium salt, and preparation method and application thereof
  • Carbamide-containing acetylated chitosan quaternary ammonium salt, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The synthetic route of urea-containing acetylated chitosan quaternary ammonium salt is as follows.

[0037]

[0038] Wherein, R is chlorophenyl or phenyl; the average degree of polymerization n ranges from 20 to 3000.

[0039] In this example, the quaternary ammonium salt of the target compound containing urea-containing acetylated chitosan was synthesized according to the above synthetic route.

[0040] 1) Preparation of chloroacetylated chitosan quaternary ammonium salt: 1.61g chitosan (see figure 1 ) in 80mL of 1-methyl-2-pyrrolidone, add 4.5g of sodium iodide, 15mL of 15% sodium hydroxide solution and 15mL of methyl iodide successively under stirring, reflux and stir at 60°C for 2h, and wait for the reaction After the end, add 1.51mL chloroacetyl chloride dropwise, react at room temperature for 24h, then precipitate with 250mL dehydrated alcohol, after suction filtration, washing, and vacuum freeze-drying, the product chloroacetylated chitosan quaternary ammoniu...

Embodiment 2

[0044] The difference from Example 1 is:

[0045] 1) Preparation of chloroacetylated chitosan quaternary ammonium salt: 1.61g chitosan (see figure 1 ) was dispersed in 80mL of 1-methyl-2-pyrrolidone, and 4.5g of sodium iodide, 15mL of 15% sodium hydroxide solution and 15mL of methyl iodide were added successively under stirring, and stirred under reflux at 60°C for 4h. After the end, add 2.265mL chloroacetyl chloride dropwise, react at room temperature for 24h, then precipitate with 300mL dehydrated alcohol, after suction filtration, washing, and vacuum freeze-drying, the product chloroacetylated chitosan quaternary ammonium salt (see figure 2 ) 3.7g, set aside.

[0046] 2) Preparation of urea: Dissolve 1.63g of triphosgene in 5mL of ethyl acetate, add dropwise 6mL of ethyl acetate solution with a concentration of 2mmol / mL 2-chloroaniline into it under ice bath, stir at room temperature for 1h, and heat at 60°C Reflux to clarification, then suspend distillation under reduce...

Embodiment 3

[0049] The difference from Example 1 is:

[0050] 1) Preparation of chloroacetylated chitosan quaternary ammonium salt: 1.61g chitosan (see figure 1 ) in 80mL of 1-methyl-2-pyrrolidone, add 4.5g of sodium iodide, 15mL of 15% sodium hydroxide solution and 15mL of methyl iodide successively under stirring, reflux and stir at 60°C for 2h, and wait for the reaction After the end, add 1.51mL chloroacetyl chloride dropwise, react at room temperature for 36h, then precipitate with 250mL dehydrated alcohol, after suction filtration, washing, and vacuum freeze-drying, the product chloroacetylated chitosan quaternary ammonium salt (see figure 2 )3.4g, for use.

[0051] 2) Preparation of urea: Dissolve 1.63g of triphosgene in 5mL of ethyl acetate, add dropwise 5mL of ethyl acetate solution with a concentration of 2mmol / mL 3-chloroaniline in an ice bath, stir at room temperature for 2h, and then dissolve at 70°C Reflux to clarification, then suspend distillation under reduced pressure ...

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Abstract

The invention relates to the fields of daily use chemicals and pharmaceutical industry, in particular to carbamide-containing acetylated chitosan quaternary ammonium salt, and a preparation method and application thereof. The preparation method of the carbamide-containing acetylated chitosan quaternary ammonium salt is characterized in that firstly, chitosan reacts with iodomethane and sodium iodide under the alkaline condition for a period of time, and then reacts with chloroacetyl chloride to obtain chloracetylated chitosan quaternary ammonium salt; then, various types of phenylamine and triphosgene react to prepare isocyanate; the isocyanate and 4-aminopyridine react to prepare carbamide; finally, the chloracetylated chitosan quaternary ammonium salt and the prepared carbamide react; through purification, the carbamide-containing acetylated chitosan quaternary ammonium salt is obtained, wherein the molar weight of the chloracetyl chloride is 1 to 2 times of that of the chitosan; the molar weight of the various types of carbamide is 2 to 3 times of that of the chloracetylated chitosan quaternary ammonium salt. The reaction is simple, convenient and efficient; the popularization is easy; the required equipment and raw materials can be easily obtained. The research shows that the derivative has good water solubility and good bacteriostatic activity; the biological activity of the chitosan is enhanced; the application range of the chitosan is enlarged; the chitosan quaternary ammonium salt can be widely applied to the fields of daily use chemicals and medicine.

Description

technical field [0001] The invention relates to the field of daily chemicals and the pharmaceutical industry, in particular to a urea-containing acetylated chitosan quaternary ammonium salt and a preparation method and application thereof. Background technique [0002] Chitosan is a deacetylated product of chitin, which is formed by condensation of 2-amino-deoxy-D-glucose through β-1,4 glycosidic bonds. Due to different raw materials and preparation methods, its relative molecular mass ranges from From thousands to millions. Chitosan is abundant in nature. It is widely found in the shells of crustaceans and arthropods, as well as in the cell walls of algae and fungi. It is the second largest natural polymer with annual output after cellulose. The only natural alkaline polysaccharide found. In recent years, chitosan's good biodegradability, biocompatibility, film-forming properties and strong antibacterial, antiseptic and fresh-keeping ability have attracted widespread atte...

Claims

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Application Information

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IPC IPC(8): C08B37/08A01N47/36A01P3/00
CPCA01N47/36C08B37/003
Inventor 郭占勇张晶晶谭文强栾芳魏丽杰王刚董方李青
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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