Compounds and formulations for protective coatings
Compositions for forming protective coatings on, e.g., agricultural products, can form a lamellar structure on the surface of the agricultural product that forms a barrier to, e.g., water and gas.
1. A method of coating an agricultural product, the method comprising:
(i) applying a mixture comprising a coating agent and a solvent to the agricultural product, wherein the coating agent comprises one or more fatty acids having a carbon chain length from 14 to 22, one or more fatty acid esters having a carbon chain length from 14 to 22, or a combination thereof; and
(ii) drying the mixture at a temperature of greater than 50° C. to form a coating on the agricultural product,
wherein the coating has a lamellar structure comprising a plurality of lamellae; and
wherein the coating provides a barrier to water transfer, gas transfer, or both.
2. A method of reducing the mass loss rate of an agricultural product, the method comprising:
(i) applying a mixture comprising a coating agent and a solvent to the agricultural product, wherein the coating agent comprises one or more fatty acids having a carbon chain length from 14 to 22, one or more fatty acid esters having a carbon chain length from 14 to 22, or a combination thereof; and
(ii) drying the mixture at a temperature of greater than 50° C. to form a coating on the agricultural product,
wherein the coating has a lamellar structure comprising a plurality of lamellae; and
wherein the coating provides a barrier to water transfer, gas transfer, or both.
3. The method of claim 1 , wherein the coating agent further comprises one or more fatty acid salts.
4. The method of claim 1 , wherein a concentration of the coating agent in the mixture is from about 25 g/L to about 60 g/L.
5. The method of claim 1 , comprising drying the mixture at a temperature from about 55° C. to about 65° C. to form the coating on the agricultural product.
6. The method of claim 1 , wherein the coating comprises a plurality of grains.
7. The method of claim 2 , wherein the coating agent comprises one or more fatty acid salts having a carbon chain length from 7 to 22.
8. The method of claim 2 , comprising drying the mixture at a temperature from about 55° C. to about 65° C. to form the coating on the agricultural product.
9. The method of claim 2 , wherein the coating comprises a plurality of grains.
10. The method of claim 3 , wherein the one or more fatty acid salts have a carbon chain length from 7 to 22.
11. The method of claim 10 , wherein the one or more fatty acid esters have a carbon chain length from 14 to 20 and the one or more fatty acid salts have a carbon chain length from 14 to 18.
12. The method of claim 1 , wherein the coating agent comprises 65 wt % to 99 wt % of a total amount of fatty acids and fatty acid esters.
13. The method of claim 12 , wherein the coating agent further comprises 1 wt % to 35 wt % of a total amount of fatty acid salts.
14. The method of claim 1 , wherein the coating agent comprises 65 wt % to 99 wt % of a total amount of one or more fatty acid esters having a carbon chain length from 14 to 20.
15. The method of 202, wherein the coating agent further comprises 1 wt % to 35 wt % of a total amount of one or more fatty acid salts having a carbon chain length from 14 to 18.
16. The method of claim 1 , wherein each fatty acid and/or ester thereof is an independently selected compound of Formula IA, wherein Formula IA is:
wherein:
R is selected from the group consisting of H and C 1 -C 6 alkyl optionally substituted with one or more of OH and C 1 -C 6 alkoxy,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently selected from the group consisting of H, OH, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, and C 1 -C 6 alkoxy,
each occurrence of R 10A , R 10B , R 11A , and R 11B is independently selected from the group consisting of H, OH, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, and C 1 -C 6 alkoxy,
or any two R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A , and R 11B on adjacent carbon atoms are taken together with the carbon atoms to which they are attached to form a double bond, a 3- to 6-membered ring heterocycle, or a C 3 -C 6 cycloalkyl,
is an integer from 0 to 17,
p is an integer from 0 to 17, and
the sum of o and p is from 9 to 17.
17. The method of claim 16 , wherein at least one of the compounds of Formula IA is a compound of Formula IA-A-i:
or a salt thereof,
wherein:
R A1 and R A2 are independently selected from H and C 1 -C 6 alkyl,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently selected from the group consisting of H, OH, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, and C 1 -C 6 alkoxy,
each occurrence of R 10A , R 10B , R 11A , and R 11B is independently selected from the group consisting of H, OH, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, and C 1 -C 6 alkoxy,
or any two R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A , and R 11B on adjacent carbon atoms are taken together with the carbon atoms to which they are attached to form a double bond, a 3- to 6-membered ring heterocycle, or a C 3 -C 6 cycloalkyl,
is an integer from 0 to 17,
p is an integer from 0 to 17, and
the sum of o and p is from 9 to 17.
18. The method of claim 16 , wherein at least one of the compounds of Formula IA is a compound of Formula IA-A-ii:
or a salt thereof,
wherein:
R A1 and R A3 are independently selected from H and C 1 -C 6 alkyl,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently selected from the group consisting of H, OH, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, and C 1 -C 6 alkoxy,
each occurrence of R 10A , R 10B , R 11A , and R 11B is independently selected from the group consisting of H, OH, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, and C 1 -C 6 alkoxy,
or any two R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A , and R 11B on adjacent carbon atoms are taken together with the carbon atoms to which they are attached to form a double bond, a 3- to 6-membered ring heterocycle, or a C 3 -C 6 cycloalkyl,
is an integer from 0 to 17,
p is an integer from 0 to 17, and
the sum of o and p is from 9 to 17.
19. The method of claim 3 , wherein each fatty acid salt is an independently selected compound of Formula IIA, wherein Formula IIA is:
wherein:
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently selected from the group consisting of H, OH, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, and C 1 -C 6 alkoxy,
each occurrence of R 10A , R 10B , R 11A , and R 11B is independently selected from the group consisting of H, OH, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, and C 1 -C 6 alkoxy,
or any two R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A , and R 11B on adjacent carbon atoms are taken together with the carbon atoms to which they are attached to form a double bond, a 3- to 6-membered ring heterocycle, or a C 3 -C 6 cycloalkyl,
is an integer from 0 to 17,
p is an integer from 0 to 17,
the sum of o and p is from 9 to 17,
X n+ is a cationic moiety having formal charge n, and
each occurrence of R′ is selected from H and C 1 -C 6 alkyl.
20. The method of claim 1 , wherein an interlayer spacing of lamellae in the plurality of lamellae is from about 3 nm to about 6 nm.
21. The method of claim 1 , wherein the coating has a thickness of about 100 nm to about 20 microns.
22. The method of claim 1 , wherein the coating has a thickness of about 100 nm to about 2 microns.
23. The method of claim 1 , wherein the solvent comprises water.
24. The method of claim 1 , wherein the mixture is dried at a temperature from about 55° C. to about 65° C. to form the coating on the agricultural product.
25. The method of claim 1 , wherein the mixture is dried at a temperature from about 60° C. to about 65° C. to form the coating on the agricultural product.
26. The method of claim 6 , wherein each grain in the plurality of grains has a grain size from about 9 nm to about 22 nm.
27. The method of claim 1 , wherein the mixture is dried at a temperature from about 55° C. to about 65° C. to form the coating on the agricultural product, and the coating comprises a plurality of grains, wherein each grain of the plurality of grains has a grain size from about 9 nm to about 22 nm.
28. The method of claim 1 , wherein drying the mixture at a temperature of greater than 50° C. to form the coating on the agricultural product reduces the probability that an orientation of the lamellae deviates from a plane that is substantially parallel to a plane of a surface of the agricultural product, thereby resulting in a lower mass loss rate and a lower respiration rate of the agricultural product compared to drying the mixture at 25° C.
29. The method of claim 6 , wherein drying the mixture at a temperature of greater than 50° C. to form the coating on the agricultural product increases a grain size of each grain in the plurality of grains, thereby resulting in a lower mass loss rate, a lower gas diffusion ratio, and a lower respiration rate of the agricultural product compared to drying the mixture at 25° C.
30. The method of claim 1 , wherein the agricultural product comprises plant matter.