Granted Patent B2

US 12,408,680 · App. 17/940,811 · Granted Sep 9, 2025

Inventors: Justin Ryan (Goleta, CA); Stanley Zhang (Goleta, CA); Charles Patrick Frazier (Goleta, CA)

Assignee: Apeel Technology, Inc.

A23B7/154A23B2/775A23B7/16C07F9/091A23V2002/00

Abstract

Claims (42)

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.

Assignments (3)

Continuity (2)

References Cited (400)