# US 12,759,969 B2 · Antimicrobial phenolic fatty acid-based epoxy curing agents for polymers

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- Number: US 12,759,969 B2
- Document ID: US12759969B2
- Status: Granted
- Kind: B2
- Application number: 18/476,728
- Filed: 2023-09-28
- Published: 2024-01-18
- Granted: 2026-10-13
- Earliest claimed: 2019-09-27
- Assignees: The United States of America as represented by the Secretary of Agriculture
- Applicants: The United States of America, as represented by the Secretary of Agriculture
- Inventors: Helen N. Lew; Kun Huang; Richard D. Ashby; Xuetong Fan
- Web page: https://patentgrep.com/patent/US12759969B2

## CPC

- C07C 231/02: from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
- A01N 43/50: 1,3-Diazoles; Hydrogenated 1,3-diazoles
- C07D 233/08: with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C08G 59/52: Amino carboxylic acids
- C07C 237/10: having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Composition and methods for killing microorganisms using antimicrobial epoxy polymers and epoxy polymer curing agents are described. Compositions containing at least one compound of formula I where R1 is a phenolic group (e.g., simple phenol, creosote, thymol, or carvacrol), and where R2 is a polyamine (e.g., ethylenediamine (EDA), diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), hexamethylenediamine (HDA)); and optionally a carrier; the compositions may additionally contain at least one epoxy resin. Methods for killing microorganisms involving contacting the microorganisms with an effective microorganism killing amount of the above composition.

## Claims

### Claim 1

A method for killing microorganisms, said method comprising contacting said microorganisms with an effective microorganism killing amount of an antimicrobial epoxy polymer comprising a curing agent with structure:
where R1 is a phenolic group, and where R2 is a polyamine group and wherein R1 in the curing agent is:

### Claim 2 (depends on 1)

The method of claim 1 wherein R2 in the polyamine group is: ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine or hexamethylenediamine.

### Claim 3 (depends on 1)

The method of claim 1 wherein the epoxy polymer is a diglycidyl ether of bisphenol A derived epoxy polymer.

### Claim 4 (depends on 1)

The method of claim 1 wherein the antimicrobial epoxy polymer is prepared by mixing an epoxy resin with the curing agent of claim 1.

### Claim 5

A method for killing microorganisms, said method comprising contacting said microorganisms with an effective microorganism killing amount of an antimicrobial epoxy polymer comprising a curing agent with structure:
where R1 is a phenolic group, and where R2 is a polyamine group, further comprising
Wherein n=0, 1 or 2.