Functionalized high-oleic soybean oil wax and emulsion for post-harvest treatment of fresh fruit

Patent metadata

Field	Value
Publication number	US-11845848-B2
Application number	US-202117244699-A
Country	US
Kind code	B2
Filing date	Apr 29, 2021
Priority date	Apr 30, 2020
Publication date	Dec 19, 2023
Grant date	Dec 19, 2023

Abstract

The present application is directed to a compound having the Formula (I):wherein R1, R2, and R3 are as described herein. The present application is also directed to a wax composition comprising a wax and a compound of Formula (I). Processes of making a wax composition and for coating a plant or plant part with the compound of Formula (I) are also described.

First claim

What is claimed:

1. A compound having the Formula (I):

wherein
R 1 is H or

R 2 is H or

R 3 is H or

R 4 is H or —OH;
R 5 is H, —OH, or ═O;

 is a point of attachment of the R 1 , R 2 , or R 3 to its respective oxygen atom in the compound of Formula (I);
is a single or a double bond;
n is an integer from 1 to 13;
m is an integer from 2 to 19;
wherein at least one of R 1 , R 2 , or R 3 is

 and
wherein when R 4 is H then R 5 is —OH or ═O;
wherein when R 5 is H then R 4 is —OH;
wherein the compound is not a hydrogenated castor oil;
with the proviso that 1) when m is 5 and n is 5, then R 4 is not OH; 2) when m is 7 and n is 7, then R 4 is not OH; 3) when m is 8 and n is 6, then R 4 is not OH; 4) when R 2 is H, R 3 is H, m is 15, and n is 5, then R 4 is not OH;
or a stereoisomer thereof.

2. The compound of claim 1 , wherein n is an integer from 3 to 7 and m is an integer from 7 to 13.

3. The compound of claim 1 , wherein m is 7 and n is 7.

4. The compound of claim 1 , wherein m is 9 and n is 5.

5. The compound of claim 1 , wherein the compound has the Formula (Ia), Formula (Ib), Formula (Ic), or Formula (Id):

6. The compound of claim 1 , wherein the compound is selected from the group consisting of

7. The compound of claim 1 , wherein the compound has the Formula (Ia), Formula (Ib), Formula (Ic), or Formula (Id):

8. A wax composition comprising:
(a) a wax; and
(b) a compound of Formula (I):

wherein
R 1 is H or

R 2 is H

R 3 is H or

R 4 is H or —OH;
R 5 is —OH, or ═O;

 is a point of attachment of the R 1 , R 2 , or R 3 to its respective oxygen atom in the compound of Formula (I);
is a single or a double bond;
n is an integer from 1 to 13;
m is an integer from 2 to 19;
wherein at least one of R 1 , R 2 , or R 3 is

 and
wherein when R 4 is H then R 5 is —OH or =0;
wherein when R 5 is H then R 4 is —OH;
wherein the compound is not a hydrogenated castor oil;
or a stereoisomer thereof,
wherein the wax and the compound of Formula (I) are mixed together.

9. The wax composition of claim 8 , wherein n is an integer from 3 to 7 and m is an integer from 7 to 13.

10. The wax composition of claim 8 , wherein the wax is selected from the group consisting of carnauba wax, beeswax, candwlilla wax, shellac resin wax, rice bran wax, sugarcane wax, and sorghum wax.

11. The wax composition of claim 8 , wherein the wax is carnauba wax.

12. The wax composition of claim 8 , wherein the compound of Formula (I) has the Formula (Ia), Formula (Ib), Formula (Ic), or Formula (Id):

13. The wax composition of claim 8 , wherein the compound of Formula (I) is selected from the group consisting of

a mixture thereof,
wherein

 indicates a bond between adjacent carbons where the —OH is bonded to one of the adjacent carbons:

14. The wax composition of claim 8 , wherein the wax ranges from 30 wt % to 99 wt % of the wax composition, and the compound of Formula (I) ranges from 70 wt % to 1 wt % of the wax composition.

15. The wax composition of claim 8 , wherein the wax ranges from 50 wt % to 90 wt % of the wax composition, and the compound of Formula (I) ranges from 50 wt % to 10 wt % of the wax composition.

16. A fruit coated with the wax composition of claim 8 .

17. A compound having the Formula (I):

wherein
R 1 is H or

R 2 is H or

R 3 is H or

R 4 is H or —OH;
R 5 is H, —OH, or ═O;

 is a point of attachment of the R 1 , R 2 , or R 3 to its respective oxygen atom in the compound of Formula (I);
is a single or a double bond;
n is 1, 2, 3, 6, 7, 8, 9, 10, 11, 12, or 13;
m is an integer from 2 to 19;
wherein at least one of R 1 , R 2 , or R 3 is

 and
wherein when R 4 is H then R 5 is —OH or ═O;
wherein when R 5 is H then R 4 is —OH;
with the proviso that 1) when m is 7 and n is 7, then R 4 is not OH; 2) when m is 8 and n is 6, then R 4 is not OH;
or a stereoisomer thereof.

18. A compound of Formula:

Assignees

• Univ Iowa State Res Found Inc
• Univ Tennessee Res Found

Inventors

• Wang Tong
• Fei Tao
• Gutierrez Francisco Miquel Ang Leyva

Classifications

• A23B2/75 Primary

  with doubly-bound oxygen · CPC title

• C08K5/11 Primary

  of acyclic polycarboxylic acids · CPC title

• A23P20/11

  Coating with compositions containing a majority of oils, fats, mono/diglycerides, fatty acids, mineral oils, waxes or paraffins · CPC title

• B01F23/40

  Mixing liquids with liquids; Emulsifying · CPC title

• C08L91/06

  Waxes · CPC title