Monomer compositions with antimicrobial functionality

Patent metadata

Field	Value
Publication number	US-10743537-B2
Application number	US-201715839199-A
Country	US
Kind code	B2
Filing date	Dec 12, 2017
Priority date	Dec 12, 2017
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

Abstract

Techniques regarding ionene compositions with antimicrobial functionality are provided. For example, one or more embodiments can comprise a monomer, which can comprise a single ionene unit. The single ionene unit can comprise a cation distributed along a molecular backbone. Also, a hydrophobic functional group can be covalently bonded to the molecular backbone, and the single ionene unit can have antimicrobial functionality.

First claim

What is claimed is:

1. A monomer comprising:
a single ionene unit comprising a nitrogen cation distributed along a molecular backbone, and a hydrophobic functional group covalently bonded to the molecular backbone, wherein the single ionene unit has antimicrobial functionality, wherein the monomer is characterized by a chemical structure selected from the group consisting of:

wherein “n” is an integer greater than or equal to one and less than or equal to one thousand.

2. The monomer of claim 1 , wherein the hydrophobic functional group is derived from an alkyl halide.

3. A method for making the monomer of claim 1 , comprising:
dissolving an amine monomer and an electrophile in a solvent, wherein the amine monomer is characterized by a first structure:

wherein “n” is an integer greater than or equal to one and less than or equal to one thousand, and wherein the electrophile is a halide compound characterized by a first formula:

wherein “X” is a halogen; and
forming a monomer from the amine monomer and the electrophile, the monomer comprising a single ionene unit, and the single ionene unit comprising a nitrogen cation distributed along a molecular backbone, and a hydrophobic functional group covalently bonded to the molecular backbone, wherein the single ionene unit has antimicrobial functionality, and wherein the monomer is characterized by second formula:

4. The method of claim 3 , wherein the forming comprises a quaternization to form the nitrogen cation, and wherein the halogen is selected from the group consisting of bromide and chloride.

5. The method of claim 4 , wherein the method further comprises:
stirring the amine monomer, the electrophile, and the solvent at a temperature greater than or equal to 15 degrees Celsius (° C.) and less than or equal to 150° C. for a defined period of time greater than or equal to 12 hours and less than or equal to 24 hours.

6. A method for making the monomer of claim 1 , comprising:
dissolving an amine monomer and an electrophile in a solvent, wherein the amine monomer is characterized by a first structure:

wherein the electrophile is a halide compound characterized by a second structure selected from the group consisting of:

wherein “X” is a halogen; and
forming a monomer from the amine monomer and the electrophile, the monomer comprising a single ionene unit, and the single ionene unit comprising a nitrogen cation distributed along a molecular backbone, and a hydrophobic functional group covalently bonded to the molecular backbone, wherein the single ionene unit has antimicrobial functionality, and wherein the monomer is characterized by a third structure selected from the group consisting of:

7. The method of claim 3 , wherein the forming comprises a quaternization to form the nitrogen cation, and wherein the halogen is selected from the group consisting of bromide and chloride.

8. The method of claim 4 , wherein the method further comprises:
stirring the amine monomer, the electrophile, and the solvent at a temperature greater than or equal to 15 degrees Celsius (° C.) and less than or equal to 150° C. for a defined period of time greater than or equal to 12 hours and less than or equal to 24 hours.

Assignees

• IBM
• Agency Science Tech & Res

Inventors

• Fevre Mareva B
• Hedrick James L
• Park Nathaniel H
• Piunova Victoria A
• Tan Pang Kern Jeremy
• Yang Yi Yan
• Zhang Mu San

Classifications

• C07D233/61

  with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms · CPC title

• C07C233/78

  with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom · CPC title

• A01N43/50

  1,3-Diazoles; Hydrogenated 1,3-diazoles · CPC title

• A01N37/30 Primary

  containing the groups —CO—N< and [IMAGE cpc-sch-A01N-0938.gif], both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof · CPC title

• A01N33/12 Primary

  Quaternary ammonium compounds · CPC title