Polymers with antimicrobial functionalities

Patent metadata

Field	Value
Publication number	US-10653142-B2
Application number	US-201715839270-A
Country	US
Kind code	B2
Filing date	Dec 12, 2017
Priority date	Dec 12, 2017
Publication date	May 19, 2020
Grant date	May 19, 2020

Abstract

Techniques regarding polymers with antimicrobial functionality are provided. For example, one or more embodiments described herein can regard a polymer, which can comprise a repeating ionene unit. The repeating ionene unit can comprise a cation distributed along a degradable backbone. The degradable backbone can comprise a terephthalamide structure. Further, the repeating ionene unit can have antimicrobial functionality.

First claim

What is claimed is:

1. A polymer comprising:
a repeating ionene unit comprising a cation distributed along a degradable backbone, and the degradable backbone comprising a terephthalamide structure, wherein the repeating ionene unit has antimicrobial functionality, and wherein the repeating ionene unit has a structure characterized by formula 1:

wherein X is the cation, wherein R is a hydrophobic functional group, wherein n is an integer greater than or equal to two and less than or equal to one thousand, and wherein Y is a functional group selected from the group consisting of an ester group and a carbonyl group.

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

3. The polymer of claim 2 , 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.

4. The polymer of claim 3 , wherein the cation is the quaternary ammonium cation.

5. The polymer of claim 3 , wherein the cation is the imidazolium cation.

6. The polymer of claim 1 , wherein the terephthalamide structure is derived from polyethylene terephthalate.

7. A method for making the polymer of claim 1 , comprising:
dissolving a plurality of amine monomers with an electrophile in a solvent, the plurality of amine monomers comprising a degradable backbone, and the degradable backbone comprising a terephthalamide structure; and
polymerizing the plurality of amine monomers and the electrophile to form a repeating ionene unit, the repeating ionene unit comprising a cation located along the degradable backbone, wherein the repeating ionene unit has antimicrobial functionality, and wherein the repeating ionene unit has a structure characterized by formula 1:

wherein X is the cation, wherein R is a hydrophobic functional group, wherein n is an integer greater than or equal to two and less than or equal to one thousand, and wherein Y is a functional group selected from the group consisting of an ester group and a carbonyl group.

8. The method of claim 7 , wherein the polymerizing covalently bonds the plurality of amine monomers together, and wherein the polymerizing forms the cation by a process selected from the group consisting of alkylation and quaternization.

9. The method of claim 8 , further comprising:
stirring the plurality of amine monomers, 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.

10. The method of claim 9 , 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.

11. A polyionene composition comprising:
a repeating ionene unit comprising:
a degradable molecular backbone comprising a terephthalamide structure; and
a cation covalently bonded to the degradable molecular backbone, wherein the repeating ionene unit has antimicrobial functionality, and wherein the repeating ionene unit has a structure characterized by formula 1:

wherein X is the cation, wherein R is a hydrophobic functional group, wherein n is an integer greater than or equal to two and less than or equal to one thousand, and wherein Y is a functional group selected from the group consisting of an ester group and a carbonyl group.

12. The polyionene composition of claim 11 , wherein the cation is selected from the group consisting of a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation and an imidazolium cation.

13. A method of forming a polymer comprising:
dissolving a plurality of degradable amine monomers with an electrophile in a solvent; and
polymerizing the plurality of degradable amine monomers and the electrophile to form a precipitate, the precipitate comprising a repeating ionene unit, the repeating ionene unit comprising a cation distributed along a degradable molecular backbone, and the degradable molecular backbone comprising a terephthalamide structure, wherein the repeating ionene unit has antimicrobial functionality, and wherein the repeating ionene unit has a structure characterized by formula 1:

wherein X is the cation, wherein R is a hydrophobic functional group, wherein n is an integer greater than or equal to two and less than or equal to one thousand, and wherein Y is a functional group selected from the group consisting of an ester group and a carbonyl group.

14. The method of claim 13 , further comprising:
preparing the plurality of degradable amine monomers through an aminolysis of polyethylene terephthalate, wherein the terephthalamide structure is derived from the polyethylene terephthalate.

15. The method of claim 14 , further comprising:
stirring the plurality of degradable amine monomers, 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, wherein the polymerizing forms the cation by a process selected from the group consisting of an alkylation and a quaternization.

Assignees

• IBM
• Agency Science Tech & Res

Inventors

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

Classifications

• C08G69/00

  Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule (products obtained from isocyanates or isothiocyanates C08G18/00; polyamide-imides C08G73/14) · CPC title

• C08G2230/00

  Compositions for preparing biodegradable polymers · CPC title

• A01N43/50 Primary

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

• A01N33/12

  Quaternary ammonium compounds · CPC title

• A01N37/22 Primary

  the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides · CPC title