IP Library › Granted Patent US 11,129,847
Granted Patent B2
US 11,129,847 · App. 16/435,559 · Granted Sep 28, 2021

Antibacterial wound dressing, method for preparing the same, and use thereof

Inventors: Junfeng Zhang (Huizhou, CN); Jinwen Mo (Huizhou, CN); Jie Dong (Huizhou, CN)
Assignee: HUIZHOU FORYOU MEDICAL DEVICES CO., LTD.
A61K31/717A61K9/0014A61L15/28A61L15/46A61P17/02
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Quick Facts
Patent No.
US 11,129,847
App. No.
16/435,559
Granted
Sep 28, 2021
Kind
B2
Abstract

An antibacterial wound dressing, a method for preparing the antibacterial wound dressing, and a use of the antibacterial wound dressing are provided. The antibacterial wound dressing is obtained by amidating carboxymethyl cellulose with a guanidine compound. The carboxymethyl cellulose has a substitution degree of 0.1-0.6, and the guanidine compound has a grafting degree of 0.2%-10.0%.

Claims (35)

1. An antibacterial wound dressing, having a structural formula I:

wherein R 1 , R 2 , R 3 and R 4 each is —OH or —OCH 2 COONa; R 5 is —CH 2 OH or —CH 2 OCH 2 COONa; R 6 is

wherein R 7 is Cl − , H 2 PO 4 − , CH 3 CH 2 COO − , or CH 2 OH(CHOH) 4 COO − , n=200-800, m=10-100; the antibacterial wound dressing is obtained by carboxymethyl cellulose and a guanidine compound, and the connection between the carboxymethyl cellulose and the guanidine compound is an amide bond; a substitution degree of the carboxymethyl cellulose is in a range of 0.1 to 0.5.

2. The antibacterial wound dressing of claim 1 , wherein n=200-500.

3. The antibacterial wound dressing of claim 1 , wherein the substitution degree of the carboxymethyl cellulose is in a range of 0.18 to 0.3, a grafting degree of the guanidine compound is ranged from 0.2% to 10.0%.

4. The antibacterial wound dressing of claim 3 , wherein the substitution degree of the carboxymethyl cellulose is ranged from 0.2 to 0.5.

5. The antibacterial wound dressing of claim 3 , wherein the guanidine compound is polyhexamethylene guanidine and a derivative thereof, or polyhexamethylene biguanide and a derivative thereof.

6. The antibacterial wound dressing of claim 5 , wherein the guanidine compound is polyhexamethylene guanidine hydrochloride, polyhexamethylene biguanide hydrochloride, polyhexamethylene guanidine phosphate, polyhexamethylene guanidine propionate, or polyhexamethylene guanidine gluconate.

7. The antibacterial wound dressing of claim 6 , wherein the grafting degree of the guanidine compound is ranged from 0.5% to 9.0%.

8. The antibacterial wound dressing of claim 7 , wherein the grafting degree of the guanidine compound is ranged from 0.5% to 5.0%.

9. The antibacterial wound dressing of claim 3 , wherein the carboxymethyl cellulose comprises one raw material selected from the group consisting of a lyocell fiber, a cotton fiber, a bamboo fiber and a viscose fiber.

10. A method for preparing an antibacterial wound dressing, comprising:

S1, alkalizing cellulose with sodium hydroxide by means of a solvent method by using water and ethanol as reaction media, such that an alkali cellulose is obtained, and etherifying the alkali cellulose with chloroacetic acid to prepare carboxymethyl cellulose having a substitution degree of 0.1-0.5;

S2, preparing a carboxymethyl cellulose-organic solvent suspension having a mass/volume ratio of 0.5%-40%;

S3, adding an activating agent or an acid regulating agent and a condensing agent into the carboxymethyl cellulose-organic solvent suspension, further adding a guanidine compound, and performing a reaction at 0° C.-50° C. for 0.5 hour-48 hours; and

S4, removing unreacted small molecular substances, and performing a drying treatment to obtain the antibacterial wound dressing;

wherein the antibacterial wound dressing has a structural formula I:

R 1 , R 2 , R 3 and R 4 each is —OH or —OCH 2 COONa; R 5 is —CH 2 OH or —CH 2 OCH 2 COONa; R 6 is

R 7 is Cl − , H 2 PO 4 − , CH 3 CH 2 COO − , or CH 2 OH(CHOH) 4 COO − , n=200-800, m=10-100; the antibacterial wound dressing is obtained by the carboxymethyl cellulose and the guanidine compound, and the connection between the carboxymethyl cellulose and the guanidine compound is an amide bond.

11. The method of claim 10 , wherein an organic solvent of the carboxymethyl cellulose-organic solvent suspension is at least one solvent selected from a group consisting of toluene, acetone, butanone, tetrahydrofuran, chloroform, dimethylacetamide, dimethylformamide, dimethyl sulfoxide, dichloromethane, chloroform, acetonitrile, and pyridine.

12. The method of claim 10 , wherein the activating agent is N-hydroxysuccinimide or 1-hydroxybenzotriazole.

13. The method of claim 10 , wherein the condensing agent is a water-soluble carbodiimide compound.

14. The method of claim 10 , wherein S3 comprises: adding the condensing agent, the activating agent, and the guanidine compound to the carboxymethyl cellulose-organic solvent suspension, and performing an amidation reaction at a temperature of 20° C.-50° C. for 30 min-240 min; wherein a mass ratio of the condensing agent, the activating agent, the guanidine compound, and the carboxymethyl cellulose is set in such a way that, the mass ratio of carboxymethyl cellulose:condensing agent:activating agent:guanidine compound is 1:(0.015-0.15):(0.01-0.1):(0.02-6).

15. The method of claim 10 , wherein S1 comprises:

mixing and reacting raw lyocell having a polymerization degree of 300-1200 with sodium hydroxide aqueous solution and ethanol at a temperature of 15° C.-40° C. for 30 min-90 min; wherein a mass ratio of the raw lyocell, the sodium hydroxide, the water, and the ethanol is 1:(0.3-3.0):(3.0-6.0):(6.0-9.0);

adding chloroacetic acid, performing a reaction at a reaction temperature of 30° C.-54° C. for 1 hour-3 hours, then heating up to perform the reaction at a temperature of 55° C.-75° C. for 1 hour-3 hours; wherein a mass ratio of the raw lyocell and the chloroacetic acid is 1:(0.2-1);

adding glacial acetic acid to perform a neutralization reaction at a temperature of 20° C.-45° C. for 30 min-90 min; wherein a mass/volume ratio of the raw lyocell to the glacial acetic acid is 1:0.25; and

performing a washing by using ethanol and water and then performing a drying treatment, such that the carboxymethyl cellulose may be obtained.

16. The method of claim 10 , wherein S2 comprises:

mixing the carboxymethyl cellulose mixed with an organic solvent, such that the carboxymethyl cellulose-organic solvent suspension having a mass/volume ratio of 0.5%-40% is prepared.

17. The method of claim 10 , wherein S4 comprises:

adding a mixed solution of ethanol and water for washing; wherein the ethanol is at the concentration of 83%-86%; the washing is performed at a temperature of 35° C.-45° C. for 20 min to remove unreacted small molecular substances; and

performing a drying treatment at 50° C. to obtain the antibacterial wound dressing.

18. The method of claim 10 , wherein the activating agent is N-hydroxysuccinimide or 1-hydroxybenzotriazole, and the condensing agent is a water-soluble carbodiimide compound.

19. The method of claim 10 , wherein the amount of the activating agent to be used is 0.1%-10% by mass of the carboxymethyl cellulose, and the amount of the condensing agent to be used is 0.15%-15% by mass of the carboxymethyl cellulose.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 10, 2019
From: ZHANG, JUNFENG; MO, JINWEN; DONG, JIE
To: HUIZHOU FORYOU MEDICAL DEVICES CO., LTD.
Reel/Frame 049413/0989 →
Continuity (2)
Continuation In Part PCTCN2017085429 · May 23, 2017
Related Publication 20190290676A1 · Sep 26, 2019