Precursor compounds for molecular coatings

Patent metadata

Field	Value
Publication number	US-10266708-B2
Application number	US-201615330403-A
Country	US
Kind code	B2
Filing date	Sep 15, 2016
Priority date	Sep 16, 2015
Publication date	Apr 23, 2019
Grant date	Apr 23, 2019

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 composition consisting of:
a compound of Formula I:

and
one or more additives, wherein at least one of the one or more additives comprises a compound of Formula II:

wherein for each formula:
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;
wherein a molar ratio of the one or more additives to the compound of Formula I is in a range of 0.1 to 1, and the composition is formulated such that coatings formed from the composition are substantially free of visible residues.

2. The composition of claim 1 , wherein a carbon chain length of the compound of Formula I is the same as a carbon chain length of the compound of Formula II.

3. The composition of claim 1 , wherein a carbon chain length of the compound of Formula I is different from a carbon chain length of the compound of Formula II.

4. The composition of claim 1 , wherein the compound of Formula I is selected from the group consisting of:

5. The composition of claim 1 , wherein the compound of Formula I is selected from the group consisting of:

6. The composition of claim 1 , wherein 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 each —H.

7. The composition of claim 1 , wherein the one or more additives comprise a first additive and a second additive different from the first additive.

8. The composition of claim 7 , wherein the first additive is a fatty acid and the second additive is the compound of Formula II.

9. The composition of claim 1 , wherein the one or more additives comprise a fatty acid having a carbon chain length that is the same as a carbon chain length of the compound of Formula I.

10. The composition of claim 1 , wherein the one or more additives comprise a fatty acid having a carbon chain length that is different from a carbon chain length of the compound of Formula I.

11. A mixture comprising a composition in a solvent, the composition consisting of:
a compound of Formula I:

and
one or more additives, wherein at least one of the one or more additives comprises a compound of Formula II:

wherein for each formula:
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;
wherein a molar ratio of the one or more additives to the compound of Formula I is in a range of 0.1 to 1, and the composition is formulated such that coatings formed from the composition are substantially free of visible residues; and
wherein the composition has a concentration in the solvent of at least 0.5 mg/mL.

12. The mixture of claim 11 , wherein the solvent comprises water or ethanol.

13. The composition of claim 1 , wherein the molar ratio of the one or more additives to the compound of Formula I is in a range of about 0.1 to about 0.5.

14. The composition of claim 13 , wherein the molar ratio of the one or more additives to the compound of Formula I is in a range of about 0.2 to about 0.4.

15. The mixture of claim 11 , wherein a carbon chain length of the compound of Formula I is the same as a carbon chain length of the compound of Formula II.

16. The mixture of claim 11 , wherein a carbon chain length of the compound of Formula I is different from a carbon chain length of the compound of Formula II.

17. The mixture of claim 11 , wherein the compound of Formula I is selected from the group consisting of:

Assignees

• Apeel Tech Inc

Inventors

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

Classifications

• C09D7/63 Primary

  organic · CPC title

• A23B5/06

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

• A23B9/14

  Coating with a protective layer; Compositions or apparatus therefor · 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

• A23B7/16

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