Precursor compounds for molecular coatings

Patent metadata

Field	Value
Publication number	US-11447646-B2
Application number	US-201815905670-A
Country	US
Kind code	B2
Filing date	Feb 26, 2018
Priority date	Sep 16, 2015
Publication date	Sep 20, 2022
Grant date	Sep 20, 2022

Abstract

Presented are compositions that can be used as protective coatings for agricultural (e.g., food) substrates. The compositions can comprise a compound of Formula I:

and an additive, wherein the variables m, n, q, r, R a , R b , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are defined herein. The protective coatings formed from the compositions can be used to prevent food spoilage due to, for instance, moisture loss, oxidation, or infection by a foreign pathogen.

First claim

The invention claimed is:

1. A method of protecting harvested produce, comprising:
providing a mixture comprising a composition in a solvent, the composition comprising:
one or more compounds of Formula II:

and one or more compounds of Formula I:

wherein the composition comprises at least 90% by mass of the one or more compounds of Formula II and the one or more compounds of Formula I, and for both Formula I and Formula II:
each R a is independently —H or —C 1 -C 6 alkyl;
each R b is independently selected from —H, —C 1 -C 6 alkyl, or —OH;
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently, at each occurrence, —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 , and R 8 are each independently, at each occurrence, —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or
R 3 and R 4 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or
R 7 and R 8 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle;
R 14 and R 15 are each independently, at each occurrence, —H, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, or —C 2 -C 6 alkynyl;
the symbol represents a single bond or a cis or trans double bond;
n is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
m is 0, 1, 2 or 3;
q is 0, 1, 2, 3, 4 or 5; and
r is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
applying the mixture to a surface of the harvested produce; and
forming a coating on the produce.

2. The method of claim 1 , wherein a thickness of the coating is greater than 0.05 microns.

3. The method of claim 2 , wherein the composition further comprises an additive selected from fatty acids, esters, amides, amines, thiols, carboxylic acids, ethers, aliphatic waxes, alcohols, organic salts, and inorganic salts.

4. The method of claim 3 , wherein the additive is an organic salt.

5. The method of claim 1 , wherein the solvent comprises water or ethanol.

6. A method of protecting an agricultural product, comprising:
providing a solution comprising a composition dissolved in a solvent, the composition comprising:
one or more compounds of Formula II:

and one or more compounds of Formula I:

wherein the composition comprises at least 90% by mass of the one or more compounds of Formula II and the one or more compounds of Formula I, and for both Formula I and Formula II:
each R a is independently —H or —C 1 -C 6 alkyl;
each R b is independently selected from —H, —C 1 -C 6 alkyl, or —OH;
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently, at each occurrence, —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 , and R 8 are each independently, at each occurrence, —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or
R 3 and R 4 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or
R 7 and R 8 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle;
R 14 and R 15 are each independently, at each occurrence, —H, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, or —C 2 -C 6 alkynyl;
the symbol represents a single bond or a cis or trans double bond;
n is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
m is 0, 1, 2 or 3;
q is 0, 1, 2, 3, 4 or 5; and
r is 0, 1, 2, 3, 4, 5, 6, 7 or 8, and
wherein the composition optionally comprises one or more additives selected from fatty acids, esters, and organic salts;
applying the solution to a surface of the agricultural product; and
removing the solvent to form a protective coating on the agricultural product, the coating having a thickness of less than 3 microns.

7. The method of claim 6 , wherein the composition further comprises an organic salt.

8. The method of claim 6 , wherein the solution further comprises a carboxylic acid.

9. The method of claim 6 , wherein the solvent comprises water or ethanol.

10. A method of protecting an agricultural product, comprising:
providing a mixture comprising a composition in a solvent, the composition comprising:
one or more compounds of Formula II:

and one or more compounds of Formula I:

wherein the composition comprises at least 90% by mass of the one or more compounds of Formula II and the one or more compounds of Formula I, and for both Formula I and Formula II:
each R a is independently —H or —C 1 -C 6 alkyl;
each R b is independently selected from —H, —C 1 -C 6 alkyl, or —OH;
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently, at each occurrence, —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 , and R 8 are each independently, at each occurrence, —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or
R 3 and R 4 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or
R 7 and R 8 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered rin

Assignees

• Apeel Tech Inc

Inventors

• Perez Louis
• Holland Chance
• Rogers James
• Kaun Stephen William
• Hernandez Carlos
• Frazier Charles Patrick

Classifications

• A01N3/00

  Preservation of plants or parts thereof, e.g. inhibiting evaporation, improvement of the appearance of leaves {or protection against physical influences such as UV radiation using chemical compositions} (preservation or chemical ripening of fruit or vegetables A23B7/00); Grafting wax · CPC title

• A23B9/14

  Coating with a protective layer; Compositions or apparatus therefor · CPC title

• A23B7/16

  Coating with a protective layer; Compositions or apparatus therefor (A23B7/08 takes precedence) · CPC title

• A23B5/06

  Coating eggs with a protective layer; Compositions or apparatus therefor · CPC title

• C09D7/63 Primary

  organic · CPC title