# US 2010/0168407 A1 · Quaternized Carboxymethyl Chitosan Derivatives and Preparation Method Thereof

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- Number: US 2010/0168407 A1
- Document ID: US20100168407A1
- Status: Published application
- Kind: A1
- Application number: 12/063,227
- Filed: 2006-07-24
- Published: 2010-07-01
- Earliest claimed: 2005-09-02
- Assignees: Institute of Oceanology, Chinese Academy of Sciences
- Inventors: Pengcheng Li; Zhanyong Guo; Song Liu; Ronge Xing; Huahua Yu; Pibo Wang; Xiaolin Chen; Cuiping Li
- Web page: https://patentgrep.com/patent/US20100168407A1

## CPC

- A01N 43/16: with oxygen as the ring hetero atom
- A61K 31/14: Quaternary ammonium compounds, e.g. edrophonium, choline (betaines A61K31/205)
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- C08B 37/003: {Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof}
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C08B: POLYSACCHARIDES; DERIVATIVES THEREOF (polysaccharides containing less than six saccharide radicals attached to each other by glycosidic linkages C07H; fermentation or enzyme-using processes C12P19/00; sugar industry C13; production of cellulose D21)

## Abstract

The invention relates to a novel kind of chitosan derivative, specifically to quaternized carboxymethyl chitosand derivatives and preparation method. Chitosan with different molecular weight reacts with chloroactic acid give rise to carboxymethyl chitosan. After reaction of Schiff based, deoxidized and quaternized, quaternized carboxymethyl chitosan is obtained. This kind of chitosan derivative have better water-solubility and better antifungal activity, which can used in the fields of medicine and agriculture.

## Claims

### Claim 1

Quaternized carboxymethyl chitosan derivatives, characteristic structure is:
wherein R is aliphatic and aromatic groups; X is I, Br or Cl; n=3-2000 (degree of polymerization).

### Claim 2 (depends on 1)

A method for the preparation of quaternized carboxymethyl chitosan derivatives according to claim 1, characterized in that:
a) Schiff bases of carboxymethyl chitosan are obtained from the reaction of active amido and aldehydes;
b) the N-substituted carboxymethyl chitosan of step a) are obtained from the reaction of Schiff bases of carboxymethyl chitosan and NaBH4;
c) quaternized carboxymethyl chitosan iodide are obtained from the reaction of the N-substituted carboxymethyl chitosan of step b) and CH3I under alkali condition;
d) quaternized carboxymethyl chitosan chloridize and quaternized carboxymethyl chitosan bromize are obtained after the quaternized carboxymethyl chitosan iodide of step c) is anion-exchanged; the degree of quaternization of this compound is 20.3-41.5%.

### Claim 3 (depends on 2)

The method according to the claim 2, characterized in that: in step a) ratio of the carboxyethyl chitosan and the aldehyde is 1:3-1:5, and the reaction time is 1-3 h.

### Claim 4 (depends on 2)

The method according to the claim 2, characterized in that: in step b) the Schiff bases of carboxymethyl chitosan is deoxidized by NaBH4, and ratio of NaBH4 and aldehyde used is 1.5:-1:3; and the reaction time is 2-4 h.

### Claim 5 (depends on 2)

The method according to the claim 2, characterized in that: in step a) the molecular weight of used chitosan is 0.16×104-80×104 with the degree of deacetylation 80-100%.

### Claim 6 (depends on 2)

The method according to the claim 2, characterized in that: in step c) the N-substituted carboxymethyl chitosan is dispersed into N-methyl-2-pyrrolidone for 12 h with stirring at room temperature, and then the pH of this mixture is adjusted to 9 by 1 mol/L NaOH; N-substituted carboxymethyl chitosan reacts with CH3I (5 fold excess to added Carboxymethyl chitosan), and the concentration of I− of this solution is adjust to 0.2 mol/L with CH3I; the reaction time is 12 h.