Reactive antibacterial compound and preparation method thereof

Patent metadata

Field	Value
Publication number	US-11044908-B2
Application number	US-202016804100-A
Country	US
Kind code	B2
Filing date	Feb 28, 2020
Priority date	Feb 6, 2015
Publication date	Jun 29, 2021
Grant date	Jun 29, 2021

Abstract

A reactive antibacterial compound and a preparation method thereof are provided herein. The reactive antibacterial compound is represented by the general formula (I) or (II):

wherein R 1 represents OCN-L-NHCOOR′, OCN-L-NHCONHR′, OCN-L-NHCOSR′, OCN-L-COOR′, or OCN-L-COONHR′. G1 represents OCN-M-NHCOOG′, OCN-M-NHCONHG′, OCN-M-NHCOSG′, OCN-M-COOG′, or OCN-M-COONHG′. L, M, R′ and G′ independently for each occurrence represent divalent alkyl and cycloalkyl having from 1 to 18 carbon atoms, optionally substituted by up to 18 heteroatoms. R 4 and G 4 independently for each occurrence represent a divalent alkyl and cycloalkyl having from 1 to 18 carbon atoms, optionally substituted by at most 18 heteroatoms. G 2 and G 3 independently for each occurrence represent —H, —F, —Cl, —Br, —I, —OCH3, —OCH2CH3, —OPr, —CN, —SCN, —NO, —NO2, a monovalent unsubstituted or substituted alkyl, cycloalkyl, or aryl having from 1 to 7 carbon atoms. Z and X independently for each occurrence represent —COO, —SO3, or —OPO2OR 5 . R 5 represents a monovalent unsubstituted or substituted alkyl, cycloalkyl, or aryl having from 1 to 6 carbon atoms.

First claim

We claim:

1. A method of producing an antibacterial material, comprising: applying an antibacterial compound including an isocyanate group to a material by reacting the isocyanate group with a functional group in the material, thus producing the antibacterial material,
wherein the antibacterial compound represented by formula (I):

wherein:
R 1 represents OCN-L-NHCOOR′, OCN-L-NHCONHR′, OCN-L-NHCOSR′, OCN-L-COOR′, or OCN-L-COONHR′;
L represents a divalent unsubstituted or substituted alkyl, cycloalkyl, or aryl having from 1 to 18 carbon atoms;
R′ represents a divalent unsubstituted or substituted alkyl, cycloalkyl, or aryl having from 1 to 18 carbon atoms;

R 2 and R 3 independently for each occurrence represent a monovalent unsubstituted or substituted alkyl, cycloalkyl, or aryl having from 1 to 18 carbon atoms;
R 4 represents a divalent unsubstituted or substituted alkyl, cycloalkyl, or aryl having from 1 to 18 carbon atoms;
Z represents —COO, —SO 3 , or —OPO 2 OR 5 ; and
R 5 represents a monovalent unsubstituted or substituted alkyl, cycloalkyl, or aryl having from 1 to 6 carbon atoms.

2. The method of claim 1 , wherein the isocyanate group is at an end of molecule of the antibacterial compound.

3. The method of claim 1 , wherein the functional group includes a hydroxyl or amino, and the material includes fiber, cotton textile, nylon, medical perfusion tube or packaging material, or food package or food preservation material.

4. The method of claim 1 , wherein the functional group includes a hydroxyl, and the material includes cotton fibers, fibrilia, polyester fibers, or poly lactic acid (PLA).

5. The method of claim 1 , wherein the functional group includes an amino, and the material includes nylon.

6. The method of claim 1 , wherein the functional group includes an amide, and the material includes wool, pashm, silk, chinlon, or aramid.

7. The method of claim 1 , wherein the R 2 and the R 3 independently for each occurrence represent —(CH 2 ) u CH 3 , and u is an integer within a range from 0 to 17.

8. The method of claim 1 , wherein the R 4 and the R′ independently for each occurrence represent —(CH 2 ) n —, and n is an integer within a range from 1 to 18.

9. The method of claim 1 , wherein the R 1 represents OCN-L-NHCOOR′ or OCN-L-NHCONHR′.

10. The method of claim 1 , wherein the L represents:

11. A method of producing an antibacterial material, comprising: applying an antibacterial compound including an isocyanate group to a material by reacting the isocyanate group with a functional group in the material, thus producing the antibacterial material,
wherein the antibacterial compound represented by formula (I):

wherein:
R 1 represents OCN-L-NHCOOR′ or OCN-L-NHCONHR′;
L represents a divalent unsubstituted or substituted alkyl, cycloalkyl, or aryl having from 1 to 18 carbon atoms;
R′ represents a divalent unsubstituted or substituted alkyl, cycloalkyl, or aryl having from 1 to 18 carbon atoms;

R 2 and R 3 independently for each occurrence represent a monovalent unsubstituted or substituted alkyl, cycloalkyl, or aryl having from 1 to 18 carbon atoms;
R 4 represents a divalent unsubstituted or substituted alkyl, cycloalkyl, or aryl having from 1 to 18 carbon atoms;
Z represents —COO, —SO 3 , or —OPO 2 OR 5 ; and
R 5 represents a monovalent unsubstituted or substituted alkyl, cycloalkyl, or aryl having from 1 to 6 carbon atoms.

12. The method of claim 11 , wherein the R 4 and the R′ independently for each occurrence represent —(CH 2 ) n —, and n is an integer within a range from 1 to 18.

13. The method of claim 11 , wherein the L represents:

14. The method of claim 11 , wherein the functional group includes a hydroxyl or amino, and the material includes fiber, cotton textile, nylon, medical perfusion tube or packaging material, or food package or food preservation material.

15. The method of claim 11 , wherein the functional group includes a hydroxyl, and the material includes cotton fibers, fibrilia, polyester fibers, or poly lactic acid (PLA).

16. The method of claim 11 , wherein the functional group includes an amino, and the material includes nylon.

17. The method of claim 11 , wherein the functional group includes an amide, and the material includes wool, pashm, silk, chinlon, or aramid.

18. A method of inhibiting growth of bacteria, comprising: contacting the bacteria with an antibacterial material, which includes an antibacterial compound bound to a material by reacting an isocyanate group of the antibacterial compound with a functional group in the material,
wherein the antibacterial compound is selected from a group consists of

19. The method of claim 18 , wherein the material includes fiber, cotton textile, nylon, medical perfusion tube or packaging material, or food package or food preservation material.

20. The method of claim 18 , wherein the bacteria includes E. coli, S. typhimurium, P. aeruginosa, S. aureas, C. albicans , sulfate reducing bacteria, Gram-positive bacteria, Gram-negative bacteria, S. epidermidis, E. faecalis, C. xerosis , or B. anthracis.

Assignees

• Univ Shenzhen

Inventors

• Chen Shiguo
• Yuan Lingjun

Classifications

• D06M13/463 Primary

  derived from monoamines · CPC title

• D06M13/432

  Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; {Carbodiimides;} Guanidines, e.g. dicyandiamides · CPC title

• D06M13/467

  derived from polyamines · CPC title

• D06M13/477

  having six-membered heterocyclic rings · CPC title

• A01N2300/00

  Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48 · CPC title