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Double modified carboxymethyl chitosan derivative and preparation method thereof

A technology of carboxymethyl chitosan and its derivatives, which is applied in the field of chemically double-modified carboxymethyl chitosan derivatives and its preparation, and can solve the problems of poor water solubility, antibacterial properties and biological compatibility of chitosan derivatives. Capacitance and other issues to achieve the effect of improving biological safety, excellent bactericidal performance, reducing pollution and energy consumption

Active Publication Date: 2017-10-31
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] It can be seen that it is difficult for chitosan derivatives prepared by a single modification method to have good water solubility, antibacterial properties and biocompatibility at the same time.

Method used

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  • Double modified carboxymethyl chitosan derivative and preparation method thereof
  • Double modified carboxymethyl chitosan derivative and preparation method thereof
  • Double modified carboxymethyl chitosan derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] A kind of quaternary ammonium salt and arginine double modified carboxymethyl chitosan derivative, its molecular structure formula is as follows:

[0060]

[0061] Wherein, x, y and z are natural numbers, 1≤x≤10000, 1≤y≤10000, 1≤z≤10000.

[0062] The concrete preparation method of above-mentioned quaternary ammonium salt and arginine carboxymethyl chitosan derivative is as follows:

[0063] Weigh 0.1g carboxymethyl chitosan (the number average molecular weight is 2×10 5 Da, carboxymethyl substitution degree is 100%, deacetylation degree is 100%) add 100mL water, obtain the solution that mass volume percent concentration is 0.1%; Add 2,3-epoxypropyltrimethylammonium chloride to carboxylate In methyl chitosan solution, react for 12 hours to obtain solution S1; activate arginine in 30mL pH 4.5 solution (the molar ratio of NHS and EDC is 1:10); pour the arginine activation solution into solution S1 , and reacted for 48 hours; adding hydroxylamine hydrochloride in an eq...

Embodiment 2

[0073] A kind of quaternary ammonium salt and oligoarginine double modified carboxymethyl chitosan derivative, its molecular structure formula is as follows:

[0074]

[0075] Wherein, x, y and z are natural numbers, 1≤x≤10000, 1≤y≤10000, 1≤z≤10000, n=5.

[0076] The concrete preparation method of above-mentioned quaternary ammonium salt and oligoarginine double modified carboxymethyl chitosan derivative is as follows:

[0077] Take by weighing 50g carboxymethyl chitosan (the number average molecular weight is 10 3Da, carboxymethyl substitution degree is 80%, deacetylation degree is 80%) add 100mL water, obtain the solution that mass volume percent concentration is 50%; Add 2,3-epoxypropyltrimethylammonium chloride to carboxy In methyl chitosan solution, react for 2 hours to obtain solution S1; activate oligoarginine in 30mL pH 6.5 solution (the molar ratio of NHS and EDC is 1:1); pour the oligoarginine activation solution into the solution S1 and react for 6 hours; add h...

Embodiment 3

[0079] A kind of quaternary ammonium salt and oligoarginine double modified carboxymethyl chitosan derivative, its molecular structure formula is as follows:

[0080]

[0081] Wherein, x, y and z are natural numbers, 1≤x≤10000, 1≤y≤10000, 1≤z≤10000, n=10.

[0082] The concrete preparation method of above-mentioned quaternary ammonium salt and oligoarginine double modified carboxymethyl chitosan derivative is as follows:

[0083] Take by weighing 30g carboxymethyl chitosan (the number average molecular weight is 10 4 Da, carboxymethyl substitution degree is 50%, deacetylation degree is 95%) add 100mL water, obtain the solution that mass volume percent concentration is 30%; Add 2,3-epoxypropyl trimethyl ammonium chloride to carboxy In methyl chitosan solution, react for 10 hours to obtain solution S1; activate oligoarginine in 30mL pH 6.0 solution (the molar ratio of NHS and EDC is 1:0.1); pour the oligoarginine activation solution into the solution S1 and react for 6 hours...

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Abstract

The invention discloses a double modified carboxymethyl chitosan derivative and a preparation method thereof. The molecular structural formula of the product is shown as formula (1), wherein x, y, z and n are natural numbers; x is more than or equal to 1 but less than or equal to 10000; y is more than or equal to 1 but less than or equal to 10000; z is more than or equal to 1 but less than or equal to 10000; and n is more than or equal to 1 but less than or equal to 30. The preparation method comprises the step of causing carboxymethyl chitosan, quaternary ammonium salt and (oligomeric) arginine to react under a catalyzing condition, thereby acquiring the double modified carboxymethyl chitosan derivative. The preparation method is mild in reaction condition, requires no high-temperature high-pressure treatment, requires no organic solvent or strong acid, is green and environment-friendly and is suitable for large-scale production. According to the invention, the quaternary ammonium salt and the (oligomeric) arginine are simultaneously grafted on a main chain of carboxymethyl chitosan, so that the derivative has excellent water solubility, antibacterial performance and biocompatibility.

Description

technical field [0001] The invention relates to the field of chemical modification of chitosan. More specifically, it relates to a chemically double-modified carboxymethyl chitosan derivative and a preparation method thereof. Background technique [0002] Chitin widely exists in lower plant fungi, shells of crustaceans such as shrimps, crabs, and insects, and cell walls of fungi. It is a natural renewable resource that is second only to cellulose in reserves in nature. The chemical name of chitosan is (1,4)-2-amino-2-deoxy-β-D-glucose, which is an alkaline polysaccharide obtained after deacetylation of chitin. Chitosan has good biocompatibility and biodegradability, as well as antibacterial properties. However, because chitosan is insoluble in water, its application in many fields is greatly limited. [0003] Chitosan can be obtained through carboxymethylation under alkaline conditions to obtain carboxymethyl chitosan (J. Adv. Drug. Deliv. Rev. 2001, 50, 591.). The intro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A01N47/44A01P1/00
Inventor 牛忠伟吴曼蒋士冬
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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