Precursor compounds for molecular coatings

Patent metadata

Field	Value
Publication number	US-12173192-B2
Application number	US-202217822934-A
Country	US
Kind code	B2
Filing date	Aug 29, 2022
Priority date	Sep 16, 2015
Publication date	Dec 24, 2024
Grant date	Dec 24, 2024

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 fatty acids, one or more compounds of Formula II:

and
one or more compounds of Formula I:

wherein, 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 over the produce.

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

one or more compounds of Formula I:

wherein the composition comprises at least 90% by mass of the one or more fatty acids, 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 over the produce.

3. The method of claim 1 , wherein one or more of the fatty acids has a carbon chain length of 4 to 24.

4. The method of claim 1 , wherein one or more of the fatty acids has a carbon chain length of 12 to 22.

5. The method of claim 1 , wherein the one or more fatty acids comprise a saturated fatty acid.

6. The method of claim 1 , wherein the one or more fatty acids comprise an unsaturated fatty acid.

7. The method of claim 1 , wherein the composition further comprises one or more organic salts.

8. The method of claim 1 , wherein a mass ratio of the one or more fatty acids to a total amount of the one or more compounds of Formula II and the one or more compounds of Formula I is about 0.1 to about 1.

9. The method of claim 1 , wherein a mass ratio of the one or more fatty acids to a total amount of the one or more compounds of Formula II and the one or more compounds of Formula I is about 0.2 to about 2.4.

10. The method of claim 1 , wherein one or more of the fatty acids has a carbon chain length that is different from a carbon chain length of one or more of the compounds of Formula II and Formula I.

11. The method of claim 1 , wherein one or more of the fatty acids has a carbon chain length that is the same as a carbon chain length of one or more of the compounds of Formula II and Formula I.

12. The method of claim 1 , wherein the coating has a thickness of about 0.05 microns to about 3 microns.

13. The method of claim 1 , wherein the coating reduces a rate of mass loss of the harvested produce by at least 10%.

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

15. The method of claim 14 , wherein the solvent comprises at least 25% water by volume.

16. The method of claim 1 , wherein a concentration of the composition in the solvent is at least about 0.5 mg/mL.

Assignees

• Apeel Tech Inc

Inventors

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

Classifications

• A23B9/14

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

• A23B5/06

  Coating eggs 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

• 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

• C09D7/63 Primary

  organic · CPC title