Large-scale methods of uniformly coating packaging surfaces with a volatile antimicrobial to preserve food freshness

Patent metadata

Field	Value
Publication number	US-12329158-B2
Application number	US-202318373376-A
Country	US
Kind code	B2
Filing date	Sep 27, 2023
Priority date	Jan 30, 2013
Publication date	Jun 17, 2025
Grant date	Jun 17, 2025

Abstract

The present application relates to large-scale methods of uniformly coating packaging surfaces with a benzoxaborole compound.

First claim

What is claimed is:

1. A method of treating a food packaging material with an antimicrobial agent, the method comprising:
administering a benzoxaborole treatment to one or more surfaces of the food packaging material, wherein the benzoxaborole treatment comprises one or more benzoxaborole compounds,
drying the one or more surfaces of the food packaging material,
placing a food product inside of the food packaging material,
wherein the one or more benzoxaborole compounds are:
i) of formula (IV), or a salt thereof:

wherein A and D together with the carbon atoms to which they are attached form a 5-, 6-, or 7-membered fused ring which may be substituted by C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, hydroxy, halogen, nitro, nitrile, amino, amino substituted by one or more C 1 -C 6 -alkyl groups, carboxy, acyl, aryloxy, carbonamido, carbonamido substituted by C 1 -C 6 -alkyl, sulfonamido or trifluoromethyl or the fused ring may link two oxaborole rings;
X is a group —CR 7 R 8 wherein R 7 and R 8 are each independently hydrogen, C 1 -C 6 -alkyl, nitrile, nitro, aryl, arylalkyl or R 7 and R 8 together with the carbon atom to which they are attached form an alicyclic ring; and
R 6 is hydrogen, C 1 -C 18 -alkyl, C 1 -C 18 -alkyl substituted by C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, hydroxy, amino, amino substituted by C 1 -C 18 -alkyl, carboxy, aryl, aryloxy, carbonamido, carbonamido substituted by C 1 -C 6 -alkyl, aryl or arylalkyl, arylalkyl, aryl, heteroaryl, cycloalkyl, C 1 -C 18 -alkyleneamino, C 1 -C 18 -alkyleneamino substituted by phenyl, C 1 -C 6 -alkoxy or C 1 -C 6 -alkylthio, carbonyl alkyleneamino or a radical of formula (V):

wherein A, D and X are as defined herein before, or

ii) formula (A):
R A -L A -G-L B -R B   (A),

wherein
each of R A and R B is independently a of R A and R B is of formula (E):

wherein each R 6 is independently hydrogen, alkyl, alkene, alkyne, haloalkyl, haloalkene, haloalkyne, alkoxy, alkeneoxy, haloalkoxy, aryl, heteroaryl, arylalkyl, arylalkene, arylalkyne, heteroarylalkyl, heteroarylalkene, heteroarylalkyne, halogen, hydroxyl, nitrile, amine, ester, carboxylic acid, ketone, alcohol, sulfide, sulfoxide, sulfone, sulfoximine, sulfilimine, sulfonamide, sulfate, sulfonate, nitroalkyl, amide, oxime, imine, hydroxylamine, hydrazine, hydrazone, carbamate, thiocarbamate, urea, thiourea, carbonate, aryloxy, or heteroaryloxy;
n=1, 2, 3, or 4;
B is boron;
X 2 =(CR 6 2 ) m where m=1 or 2;

each of L A and L B is independently —O— or

each of R and R′ is independently hydrogen, unsubstituted or substituted C 1-18 -alkyl, arylalkyl, aryl, or heterocyclic moiety; and
G is a substituted or unsubstituted C 1-18 -alkylene, arylalkylene, arylene, or heterocyclic moiety; and acceptable salts thereof.

2. The method of claim 1 , wherein the food product is selected from the group consisting of a strawberry, a raspberry, a blackberry, and a blueberry.

3. The method of claim 1 , wherein the benzoxaborole is of formula (IV), or a salt thereof:

wherein A and D together with the carbon atoms to which they are attached form a 5-, 6-, or 7-membered fused ring which may be substituted by C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, hydroxy, halogen, nitro, nitrile, amino, amino substituted by one or more C 1 -C 6 -alkyl groups, carboxy, acyl, aryloxy, carbonamido, carbonamido substituted by C 1 -C 6 -alkyl, sulfonamido or trifluoromethyl or the fused ring may link two oxaborole rings;
X is a group —CR 7 R 8 wherein R 7 and R 8 are each independently hydrogen, C 1 -C 6 -alkyl, nitrile, nitro, aryl, arylalkyl or R 7 and R 8 together with the carbon atom to which they are attached form an alicyclic ring; and
R 6 is hydrogen, C 1 -C 18 -alkyl, C 1 -C 18 -alkyl substituted by C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, hydroxy, amino, amino substituted by C 1 -C 18 -alkyl, carboxy, aryl, aryloxy, carbonamido, carbonamido substituted by C 1 -C 6 -alkyl, aryl or arylalkyl, arylalkyl, aryl, heteroaryl, cycloalkyl, C 1 -C 18 -alkyleneamino, C 1 -C 18 -alkyleneamino substituted by phenyl, C 1 -C 6 -alkoxy or C 1 -C 6 -alkylthio, carbonyl alkyleneamino or a radical of formula (V):

wherein A, D and X are as defined herein before.

4. The method of claim 3 , wherein the benzoxaborole compound is has the structure

or a salt thereof.

5. The method of claim 1 , wherein the benzoxaborole has the structure formula (A):
R A -L A -G-L B -R B   (A),

wherein
each of R A and R B is independently a of R A and R B is of formula (E):

wherein each R 6 is independently hydrogen, alkyl, alkene, alkyne, haloalkyl, haloalkene, haloalkyne, alkoxy, alkeneoxy, haloalkoxy, aryl, heteroaryl, arylalkyl, arylalkene, arylalkyne, heteroarylalkyl, heteroarylalkene, heteroarylalkyne, halogen, hydroxyl, nitrile, amine, ester, carboxylic acid, ketone, alcohol, sulfide, sulfoxide, sulfone, sulfoximine, sulfilimine, sulfonamide, sulfate, sulfonate, nitroalkyl, amide, oxime, imine, hydroxylamine, hydrazine, hydrazone, carbamate, thiocarbamate, urea, thiourea, carbonate, aryloxy, or heteroaryloxy;
n=1, 2, 3, or 4;
B is boron;
X 2 =(CR 6 2 ) m where m=1 or 2;

each of L A and L B is independently —O— or

each of R and R′ is independently hydrogen, unsubstituted or substituted C 1-18 -alkyl, arylalkyl, aryl, or heterocyclic moiety; and
G is a substituted or unsubstituted C 1-18 -alkylene, arylalkylene, arylene, or heterocyclic moiety; and acceptable salts thereof.

6. The method of claim 3 , wherein the benzoxaborole has the structure

or a salt thereof.

7. The method of claim 1 , wherein administering the benzoxaborole treatment to food packaging material comprises embedding the benzoxaborole compound into the food packaging material, impregnating the food packaging material with the benzoxaborole compound, or coating the food packaging material with the benzoxaborole compound.

8. The method of claim 1 , wherein the food packaging material is a chamber.

9. The method of claim 8 , wherein the chamber is a clamshell.

10. The method of claim 9 , wherein the clamshell comprises polyethylene terephthalate.

11. A large-scale method of treating a plurality of chambers with an antimicrobial agent, the method comprising:
placing a plurality of chambers in a position to be treated wherein each of the chambers comprise one or more surfaces,
administering the antimicrobial treatment to one or more surfaces of the plurality of chambers during preformation, formation, or post

Assignees

• Agrofresh Inc

Inventors

• Maclean Daniel
• Jacobson Richard M
• Malefyt Timothy

Classifications

• A23B2/721

  in a controlled atmosphere comprising other gases in addition to CO2, N2, O2 or H2O · CPC title

• A23B7/152

  in a controlled atmosphere comprising other gases in addition to CO2, N2, O2 or H2O {; Elimination of such other gases} · CPC title

• A01N55/00

  Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur (containing organo-phosphorus compounds A01N57/00) · CPC title

• A23B4/16

  in the form of gases, e.g. fumigation; Compositions or apparatus therefor · CPC title

• A23B4/20

  Organic compounds; Microorganisms; Enzymes · CPC title