Vegetable oil-based material as a substitute for carnauba wax

Patent metadata

Field	Value
Publication number	US-11827583-B2
Application number	US-202217700933-A
Country	US
Kind code	B2
Filing date	Mar 22, 2022
Priority date	Mar 22, 2017
Publication date	Nov 28, 2023
Grant date	Nov 28, 2023

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 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 0 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 0 or 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),

wherein said providing one or more monoamide compounds having the Formula (IV) comprises:
providing one or more saturated free fatty acids having the Formula (VI):

wherein R 1 is a substituted or unsubstituted C 3 to C 50 alkyl;
providing a diamine compound having the Formula (VII):

(VII), wherein n 1 is an integer from 0 to 10; and
reacting the diamine compound having the Formula (VII) with the one or more saturated free fatty acids having the Formula (VI) to form the one or more monoamide compounds of Formula (IV).

2. The process of claim 1 , wherein the one or more saturated free fatty acids having the Formula (VI) are prepared from a fully hydrogenated vegetable oil.

3. The process of claim 2 , wherein the fully hydrogenated vegetable oil is selected from the group consisting of fully hydrogenated soybean oil, fully hydrogenated cottonseed oil, fully hydrogenated sunflower oil, fully hydrogenated canola oil, fully hydrogenated corn oil, fully hydrogenated palm oil, fully hydrogenated olive oil, fully hydrogenated peanut oil, fully hydrogenated safflower oil, fully hydrogenated coconut oil, fully hydrogenated rapeseed oil, fully hydrogenated castor oil, fully hydrogenated mustard seed oil, fully hydrogenated tallow oil, fully hydrogenated bone oil, fully hydrogenated fish oil, fully hydrogenated tall oil, and a mixture thereof.

4. The process of claim 3 , wherein the fully hydrogenated vegetable oil is fully hydrogenated soybean oil.

5. The process of claim 1 , wherein the diamine compound of Formula (VII) to the one or more saturated free fatty acid of Formula (VI) molar ratio ranges from 1:1 to 1:2.

Assignees

• Univ Iowa State Res Found Inc

Inventors

• Wang Tong
• Fei Tao

Classifications

• C07C237/12 Primary

  having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups (peptides C07K) · CPC title

• C07C231/02

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · 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

• C08L91/06

  Waxes · CPC title

• 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