Compounds and formulations for protective coatings

Patent metadata

Field	Value
Publication number	US-12408680-B2
Application number	US-202217940811-A
Country	US
Kind code	B2
Filing date	Sep 8, 2022
Priority date	Sep 8, 2021
Publication date	Sep 9, 2025
Grant date	Sep 9, 2025

Abstract

The present disclosure relates to protective coatings e.g., on agricultural products, that can include a glycerophospholipid bilayer structure formed on the surface of the agricultural product.

First claim

What is claimed is:

1. A method of reducing the ripening rate of an agricultural product, the method comprising:
applying a solution comprising a coating agent to a surface of the agricultural product, wherein the coating agent comprises one or more glycerophospholipids, a temperature of the solution is between 10° C. and 80° C., and a total concentration of the one or more glycerophospholipids in the solution is between 100 g/L and 150 g/L; and
drying the solution on the surface of the agricultural product under a flow of air having a temperature between 20° C. and 100° C. to promote self-assembly of a multiplicity of glycerophospholipid bilayers on the surface of the agricultural product, thereby forming a coating on the agricultural product.

2. The method of claim 1 , wherein the one or more glycerophospholipids comprise one or more of phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and phosphatidic acid.

3. The method of claim 1 , wherein the one or more glycerophospholipids comprise one or more compounds of Formula I:

wherein:
R 1 is —H or one of the following fragments:

and
R 2 and R 3 are each independently, at each occurrence, —H or a fragment represented by Formula II:

wherein:
R 4 , R 5 , R 8 , R 9 , R 12 , R 13 , R 14 , R 15 and R 16 are each independently, at each occurrence, —H, —OH, —OR 17 or C 1 -C 6 alkyl;
R 6 , R 7 , R 10 , and R 11 are each independently, at each occurrence, —H, —OR 17 , or C 1 -C 6 alkyl; and/or
R 4 and R 5 can combine with the carbon atoms to which they are attached to form C═O; and/or
R 8 and R 9 can combine with the carbon atoms to which they are attached to form C═O; and/or
R 12 and R 13 can combine with the carbon atoms to which they are attached to form C═O; and
R 17 is at each occurrence a C 1 -C 6 alkyl,
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.

4. The method of claim 3 , wherein the fragment represented by Formula II is one of:

5. The method of claim 1 , wherein the one or more glycerophospholipids comprise phosphatidylcholine, phosphatidylethanolamine, and phosphatidylinositol.

6. The method of claim 5 , wherein the one or more glycerophospholipids comprise 20 wt % to 40 wt % phosphatidylcholine, 20 wt % to 40 wt % phosphatidylethanolamine, and 20 wt % to 40 wt % phosphatidylinositol.

7. The method of claim 5 , wherein the one or more glycerophospholipids further comprise phosphatidylserine.

8. The method of claim 1 , wherein the solution further comprises a phytosterol.

9. The method of claim 8 , wherein a weight ratio of the phytosterol to a total amount of the one or more glycerophospholipids is less than 0.05.

10. The method of claim 1 , wherein the solution is an aqueous solution.

11. The method of claim 1 , wherein a temperature of the air is between 50° C. and 100° C.

12. The method of claim 1 , wherein the multiplicity of glycerophospholipid bilayers comprise one or more open bilayers.

13. The method of claim 12 , wherein the one or more open bilayers are lamellar.

14. The method of claim 1 , wherein the multiplicity of glycerophospholipid bilayers comprise one or more closed bilayers.

15. The method of claim 14 , wherein one or more of the closed bilayers are cylindrical.

16. The method of claim 14 , wherein one or more of the closed bilayers are spherical.

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

18. A method of preparing an agricultural product having a coating disposed thereon, the method comprising:
applying a solution comprising a coating agent to a surface of the agricultural product, wherein the coating agent comprises one or more glycerophospholipids, a temperature of the solution is between 10° C. and 80° C., and a total concentration of the one or more glycerophospholipids in the solution is between 100 g/L and 150 g/L; and
drying the solution on the surface of the agricultural product under a flow of air having a temperature between 20° C. and 100° C. to promote self-assembly of a multiplicity of glycerophospholipid bilayers on the surface of the agricultural product, thereby forming a coating on the agricultural product.

19. A coated agricultural product comprising:
an agricultural product; and
a coating on the surface of the agricultural product, wherein the coating comprises one or more glycerophospholipids,
wherein the coating has a hexagonal cylindrical phase structure comprising repeating cylindrical units arranged on a hexagonal close-packed lattice on the surface of the structure, and the coating is applied to the surface of the agricultural product as a solution comprising one or more glycerophospholipids in a total concentration between 100 g/L and 150 g/L.

Assignees

• Apeel Tech Inc

Inventors

• Ryan Justin
• Zhang Stanley
• Frazier Charles Patrick

Classifications

• A23B2/775

  Organic compounds containing phosphorus · CPC title

• C07F9/091

  with hydroxyalkyl compounds with further substituents on alkyl · CPC title

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title

• A23B7/16

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

• A23B2/762

  Organic compounds containing nitrogen · CPC title