Antimicrobial polymers capable of supramolecular assembly

Patent metadata

Field	Value
Publication number	US-11617367-B2
Application number	US-202117215700-A
Country	US
Kind code	B2
Filing date	Mar 29, 2021
Priority date	Dec 12, 2017
Publication date	Apr 4, 2023
Grant date	Apr 4, 2023

Abstract

Techniques regarding chemical compounds with antimicrobial functionality are provided. For example, one or more embodiments describe herein can comprise a monomer that can comprise a molecular backbone. The molecular backbone can comprise a bis(urea)guanidinium structure covalently bonded to a functional group, which can comprise a radical. Also, the monomer can have supramolecular assembly functionality.

First claim

What is claimed is:

1. A method for making a chemical compound, comprising:
dissolving an amine monomer with an electrophile in a solvent, the amine monomer comprising a molecular backbone, and the molecular backbone comprising a bis(urea)guanidinium structure; and
polymerizing the amine monomer and the electrophile to form the chemical compound comprising an ionene unit, the ionene unit comprising a cation located along the molecular backbone.

2. The method of claim 1 , wherein the ionene unit has antimicrobial functionality.

3. The method of claim 1 , wherein the cation is selected from the group consisting of a nitrogen cation and a phosphorus cation.

4. The method of claim 1 , wherein the cation is a nitrogen cation selected from the group consisting of a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation and an imidazolium cation.

5. The method of claim 1 , wherein the cation is covalently bonded to a hydrophobic functional group.

6. The method of claim 1 , further comprising:
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 period of time greater than or equal to 8 hours and less than or equal to 72 hours.

7. The method of claim 6 , wherein the polymerizing comprises a process to form the cation, and wherein the process is selected from the group consisting of an alkylation and a quaternization.

8. The method of claim 7 , wherein the electrophile is a dialkyl halide, wherein the solvent is an organic solvent, and wherein the cation is a nitrogen cation selected from the group consisting of a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation and an imidazolium cation.

9. The method of claim 1 , wherein the ionene unit has a structure characterized by Formula 1:

wherein X 1 represents the cation, wherein R represents a hydrophobic functional group, wherein n represents an integer greater than or equal to one and less than or equal to one thousand, and wherein L 1 represents a linkage group selected from the group consisting of an alkyl group and an aryl group.

10. A method for making a copolymer, comprising:
dissolving a first amine monomer, a second amine monomer, and an electrophile in solvent, the first amine monomer comprising a molecular backbone, the molecular backbone comprising a bis(urea)guanidinium structure, the second amine monomer comprising a degradable backbone, and the degradable backbone comprising a terephthalamide structure; and
polymerizing the first amine monomer and the second amine monomer with the electrophile to form the copolymer, the copolymer comprising a first cation distributed along the molecular backbone and a second cation distributed along the degradable backbone.

11. The method of claim 10 , wherein the copolymer has antimicrobial functionality.

12. The method of claim 10 , further comprising:
stirring the first amine monomer, the second 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 period of time greater than or equal to 8 hours and less than or equal to 72 hours.

13. The method of claim 12 , wherein the polymerizing comprises a first process to form the first cation selected from the first group consisting of a first alkylation and a first quaternization.

14. The method of claim 13 , wherein the electrophile is a dialkyl halide, wherein the solvent is an organic solvent, and wherein the first cation is a nitrogen cation selected from the second group consisting of a first protonated secondary amine cation, a first protonated tertiary amine cation, a first quaternary ammonium cation and a first imidazolium cation.

15. The method of claim 13 , wherein the polymerizing further comprises a second process to form the second cation selected from the second group consisting of a second alkylation and a second quaternization.

16. The method of claim 15 , wherein the electrophile is a dialkyl halide, wherein the solvent is an organic solvent, and wherein the second cation is a nitrogen cation selected from the second group consisting of a second protonated secondary amine cation, a second protonated tertiary amine cation, a second quaternary ammonium cation and a second imidazolium cation.

17. The method of claim 10 , wherein the electrophile is a dialkyl halide and wherein the solvent is an organic solvent.

18. The method of claim 10 , wherein the copolymer has a structure characterized by Formula 1:

wherein X 1 represents the first cation, wherein R represents a hydrophobic functional group, wherein n represents an integer greater than or equal to one and less than or equal to one thousand, and wherein L 1 represents a linkage group selected from the first group consisting of an alkyl group and an aryl group; and
wherein X 2 represents the second cation, wherein m represents a second integer greater than or equal to one and less than or equal to one thousand, and wherein L 2 represents a second linkage group selected from the second group consisting of a second alkyl group and a second aryl group.

19. The method of claim 10 , wherein the copolymer has a structure characterized by Formula 1:

wherein n represents a first integer greater than or equal to one and less than or equal to one thousand; and
wherein m represents a second integer greater than or equal to one and less than or equal to one thousand.

20. The method of claim 10 , wherein the copolymer has a structure characterized by Formula 1:

wherein n represents a first integer greater than or equal to one and less than or equal to one thousand; and
wherein m represents a second integer greater than or equal to one and less than or equal to one thousand.

Assignees

• IBM
• Agency Science Tech & Res

Inventors

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

Classifications

• C08G73/0273

  Polyamines containing heterocyclic moieties in the main chain · CPC title

• A01N37/26

  containing the group [IMAGE cpc-sch-A01N-0936.gif]; Thio analogues thereof · CPC title

• A01N43/50

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

• A61Q17/005

  Antimicrobial preparations · CPC title

• C08G73/06

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule · CPC title