US 12,329,158 B2
Large-scale methods of uniformly coating packaging surfaces with a volatile antimicrobial to preserve food freshness
Daniel MacLean, Woodland, CA (US); Richard M. Jacobson, Chalfont, PA (US); and Timothy Malefyt, Stroudsburg, PA (US)
Assigned to AGROFRESH INC., Philadelphia, PA (US)
Filed by AGROFRESH INC., Philadelphia, PA (US)
Filed on Sep. 27, 2023, as Appl. No. 18/373,376.
Application 14/182,793 is a division of application No. 13/945,577, filed on Jul. 18, 2013, granted, now 8,669,207, issued on Mar. 11, 2014.
Application 18/373,376 is a continuation of application No. 17/346,446, filed on Jun. 14, 2021, granted, now 11,771,089.
Application 17/346,446 is a continuation of application No. 16/707,516, filed on Dec. 9, 2019, granted, now 11,039,617, issued on Jun. 22, 2021.
Application 16/707,516 is a continuation in part of application No. 16/123,735, filed on Sep. 6, 2018, granted, now 10,765,117, issued on Sep. 8, 2020.
Application 16/123,735 is a continuation of application No. 15/445,247, filed on Feb. 28, 2017, granted, now 10,070,649, issued on Sep. 11, 2018.
Application 15/445,247 is a continuation in part of application No. 14/690,929, filed on Apr. 20, 2015, granted, now 9,585,396, issued on Mar. 7, 2017.
Application 14/690,929 is a continuation in part of application No. 14/294,057, filed on Jun. 2, 2014, granted, now 9,426,996, issued on Aug. 30, 2016.
Application 14/294,057 is a continuation of application No. 14/167,093, filed on Jan. 29, 2014, granted, now 9,138,001, issued on Sep. 22, 2015.
Application 14/690,929 is a continuation in part of application No. 14/182,793, filed on Feb. 18, 2014, granted, now 9,138,002, issued on Sep. 22, 2015.
Application 16/707,516 is a continuation in part of application No. 15/485,500, filed on Apr. 12, 2017, abandoned.
Claims priority of provisional application 61/991,821, filed on May 12, 2014.
Claims priority of provisional application 61/758,313, filed on Jan. 30, 2013.
Claims priority of provisional application 61/831,187, filed on Jun. 5, 2013.
Claims priority of provisional application 62/323,247, filed on Apr. 15, 2016.
Prior Publication US 2024/0049714 A1, Feb. 15, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. A01N 55/08 (2006.01); A01N 25/18 (2006.01); A01N 55/00 (2006.01); A23B 2/721 (2025.01); A23B 4/16 (2006.01); A23B 4/20 (2006.01); A23B 7/152 (2006.01); A23B 7/154 (2006.01); A61K 9/00 (2006.01); A61K 9/70 (2006.01); A61K 31/69 (2006.01)
CPC A01N 55/08 (2013.01) [A01N 25/18 (2013.01); A01N 55/00 (2013.01); A23B 2/721 (2025.01); A23B 4/16 (2013.01); A23B 4/20 (2013.01); A23B 7/152 (2013.01); A23B 7/154 (2013.01); A61K 9/0034 (2013.01); A61K 9/70 (2013.01); A61K 31/69 (2013.01)] 20 Claims
 
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:

OG Complex Work Unit Chemistry
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 C1-C6-alkyl, C1-C6-alkoxy, hydroxy, halogen, nitro, nitrile, amino, amino substituted by one or more C1-C6-alkyl groups, carboxy, acyl, aryloxy, carbonamido, carbonamido substituted by C1-C6-alkyl, sulfonamido or trifluoromethyl or the fused ring may link two oxaborole rings;
X is a group —CR7R8 wherein R7 and R8 are each independently hydrogen, C1-C6-alkyl, nitrile, nitro, aryl, arylalkyl or R7 and R8 together with the carbon atom to which they are attached form an alicyclic ring; and
R6 is hydrogen, C1-C18-alkyl, C1-C18-alkyl substituted by C1-C6-alkoxy, C1-C6-alkylthio, hydroxy, amino, amino substituted by C1-C18-alkyl, carboxy, aryl, aryloxy, carbonamido, carbonamido substituted by C1-C6-alkyl, aryl or arylalkyl, arylalkyl, aryl, heteroaryl, cycloalkyl, C1-C18-alkyleneamino, C1-C18-alkyleneamino substituted by phenyl, C1-C6-alkoxy or C1-C6-alkylthio, carbonyl alkyleneamino or a radical of formula (V):

OG Complex Work Unit Chemistry
wherein A, D and X are as defined herein before, or
ii) formula (A):
RA-LA-G-LB-RB  (A),
wherein
each of RA and RB is independently a of RA and RB is of formula (E):

OG Complex Work Unit Chemistry
wherein each R6 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;
X2=(CR62)m where m=1 or 2;
each of LA and LB is independently —O— or

OG Complex Work Unit Chemistry
each of R and R′ is independently hydrogen, unsubstituted or substituted C1-18-alkyl, arylalkyl, aryl, or heterocyclic moiety; and
G is a substituted or unsubstituted C1-18-alkylene, arylalkylene, arylene, or heterocyclic moiety; and acceptable salts thereof.