Vegetable oil-based material as a substitute for carnauba wax

Patent metadata

Field	Value
Publication number	US-10851046-B2
Application number	US-201815926203-A
Country	US
Kind code	B2
Filing date	Mar 20, 2018
Priority date	Mar 22, 2017
Publication date	Dec 1, 2020
Grant date	Dec 1, 2020

Abstract

This invention relates to a wax composition comprising a plurality of fatty acid amide compounds having the Formula (I):

where R 1 , R 2 , n 1 , n 2 , m 1 , and m 2 are as described herein. This invention also relates to a wax composition comprising:
a) one or more fatty acid amide compounds having the Formula (II):

and
b) one or more fatty acid amide compounds having the Formula (III):

where R 1 , R 2 , n 1 , and n 2 are as described herein. This invention also relates to a fatty acid amide compound having the Formula (I) and a process for preparing a compound of Formula (I).

First claim

What is claimed is:

1. A fatty acid amide compound having the Formula (I):

wherein:
R 1 is a substituted or unsubstituted C 3 to C 50 alkyl or substituted or unsubstituted aryl;
R 2 is H, substituted or unsubstituted C 3 to C 50 alkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted arylalkenyl, or substituted or unsubstituted aryl;
n 1 is an integer from 1 to 10;
n 2 is an integer from 1 to 20;
m 1 is 0 or 1; and
m 2 is 0 or 1, and
wherein m 1 +m 2 cannot be 2,

wherein if R 1 is a substituted C 3 to C 50 alkyl, then R 2 is H, unsubstituted C 3 to C 50 alkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted arylalkenyl, substituted or unsubstituted aryl, or C 3 to C 50 alkyl substituted with alkyl, halogen, haloalkyl, hydroxy, lower alkoxy, carboxy, carboalkoxy, carboxamido, cyano, carbonyl, nitro, amino, alkylamino, dialkylamino, mercapto, alkylthio, sulfoxide, sulfone, acylamino, amidino, phenyl, benzyl, heteroaryl, phenoxy, benzyloxy, or heteroaryloxy; or
wherein if R 2 is a substituted C 3 to C 50 alkyl, then R 1 is an unsubstituted C 3 to C 50 alkyl, substituted or unsubstituted aryl, or C 3 to C 50 alkyl substituted with alkyl, halogen, haloalkyl, hydroxy, lower alkoxy, carboxy, carboalkoxy, carboxamido, cyano, carbonyl, nitro, amino, alkylamino, dialkylamino, mercapto, alkylthio, sulfoxide, sulfone, acylamino, amidino, phenyl, benzyl, heteroaryl, phenoxy, benzyloxy, or heteroaryloxy.

2. The fatty acid amide compound of claim 1 , wherein m 1 is 0; m 2 is 0; and R 2 is H.

3. The fatty acid amide compound of claim 1 , wherein m 1 is 0; m 2 is 1; and R 2 is a substituted or unsubstituted C 3 to C 50 alkyl, substituted or unsubstituted arylalkyl, or substituted or unsubstituted arylalkenyl.

4. The fatty acid amide compound of claim 1 , wherein m 1 is 1; m 2 is 0; and R 2 is a substituted or unsubstituted C 3 to C 50 alkyl.

5. The fatty acid amide compound of claim 1 , wherein n 2 is an integer from 6 to 12.

6. A wax composition comprising a plurality of fatty acid amide compounds having the Formula (I):

wherein:
R 1 a substituted or unsubstituted C 3 to C 50 alkyl or substituted or unsubstituted aryl;
R 2 is H, substituted or unsubstituted C 3 to C 50 alkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted arylalkenyl, or substituted or unsubstituted aryl;
n 1 is an integer from 1 to 10;
n 2 is an integer from 1 to 20;
m 1 is 0 or 1; and
m 2 is 0 or 1, and
wherein m 1 +m 2 cannot be 2,

wherein if R 1 is a substituted C 3 to C 50 alkyl, then R 2 is H, unsubstituted C 3 to C 50 alkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted arylalkenyl, substituted or unsubstituted aryl, or C 3 to C 50 alkyl substituted with alkyl, halogen, haloalkyl, hydroxy, lower alkoxy, carboxy, carboalkoxy, carboxamido, cyano, carbonyl, nitro, amino, alkylamino, dialkylamino, mercapto, alkylthio, sulfoxide, sulfone, acylamino, amidino, phenyl, benzyl, heteroaryl, phenoxy, benzyloxy, or heteroaryloxy; or
wherein if R 2 is a substituted C 3 to C 50 alkyl, then R 1 is an unsubstituted C 3 to C 50 alkyl, substituted or unsubstituted aryl, or C 3 to C 50 alkyl substituted with alkyl, halogen, haloalkyl, hydroxy, lower alkoxy, carboxy, carboalkoxy, carboxamido, cyano, carbonyl, nitro, amino, alkylamino, dialkylamino, mercapto, alkylthio, sulfoxide, sulfone, acylamino, amidino, phenyl, benzyl, heteroaryl, phenoxy, benzyloxy, or heteroaryloxy.

7. The wax composition of claim 6 , wherein the wax composition comprises compounds of Formula (I) wherein m 1 is 0; m 2 is 0; and R 2 is H.

8. The wax composition of claim 6 , wherein the wax composition comprises compounds of Formula (I) wherein m 1 is 0; m 2 is 1; and R 2 is a substituted or unsubstituted C 3 to C 50 alkyl, substituted or unsubstituted arylalkyl, or substituted or unsubstituted arylalkenyl.

9. The wax composition of claim 6 , wherein the wax composition comprises compounds of Formula (I) wherein m 1 is 1; m 2 is 0; and R 2 is a substituted or unsubstituted C 3 to C 50 alkyl.

10. The wax composition of claim 6 , wherein the wax composition comprises compounds of Formula (I) wherein n 2 is an integer from 6 to 12.

11. The wax composition of claim 6 , wherein the wax composition has a melting point ranging from 50° C. to 200° C.

12. The wax composition of claim 6 , wherein the wax composition has a penetration hardness of 3.0 mm or below, measured by a standard needle penetration test according to the ASTM D1321 standard, with a 100 g cone and the penetration being conducted for 5 seconds at 23° C.

13. The wax composition of claim 6 , further comprising one or more natural waxes.

14. A coated material comprising:
a substrate and
the wax composition of claim 6 coated on said substrate.

15. A process for preparing a compound of Formula (I):

said process comprising:
providing one or more monoamide compounds having the Formula (IV):

providing one or more acids having the Formula (Va) or Formula (Vb)

wherein
R 1 is a substituted or unsubstituted C 3 to C 50 alkyl;
R 2 is substituted or unsubstituted C 3 to C 50 alkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted arylalkenyl, or substituted or unsubstituted aryl;
R 2′ is substituted or unsubstituted C 3 to C 50 alkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted arylalkenyl, or substituted or unsubstituted aryl;
n 1 is an integer from 1 to 10;
n 2 is an integer from 1 to 20;
m 1 is 0 or 1; and
m 2 is 0 or 1,
wherein m 1 +m 2 cannot be 2, and
reacting the one or more monoamide compounds having the Formula (IV) with the one or more acids having Formula (Va) or Formula (Vb) under conditions effective to make the compound of Formula (I).

Assignees

• Univ Iowa State Res Found Inc

Inventors

• Wang Tong
• Fei Tao

Classifications

• C11C3/00 Primary

  Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom (sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F) · CPC title

• C07C233/40

  having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings · CPC title

• C11C3/12

  by hydrogenation · CPC title

• C11C3/04

  by esterification of fats or fatty oils · CPC title

• C11C3/003

  by esterification of fatty acids with alcohols (C11C3/02 takes precedence) · CPC title