Natural oil derivatives including primary amine functional groups

Patent metadata

Field	Value
Publication number	US-9611443-B2
Application number	US-201614992360-A
Country	US
Kind code	B2
Filing date	Jan 11, 2016
Priority date	Mar 13, 2013
Publication date	Apr 4, 2017
Grant date	Apr 4, 2017

Abstract

A compound has Structure I:

where R 1 and R 2 independently are C 2 -C 12 alkyl groups, X 1 is a C 4 -C 28 alkyl or alkenyl group, and R 3 is H or is a bis(aminoalkyl)amide group having Structure II:

where R 4 and R 5 independently are C 2 -C 12 alkyl groups. The compound may be a reaction product of a metathesized natural oil and a bis(aminoalkyl)amine.

First claim

What is claimed is:

1. A polymer, which comprises constitutional units formed from a reaction mixture comprising: (a) a monomer having two or more epoxy groups; and (b) a compound according to Structure I:

wherein:
R 1 and R 2 independently are C 2 -C 12 alkyl groups;
X 1 is a C 4 -C 28 alkyl group or a C 4 -C 28 alkenyl group; and
R 3 is a hydrogen atom or a bis(aminoalkyl)amide group according to Structure II:

wherein R 4 and R 5 independently are C 2 -C 12 alkyl groups.

2. The polymer of claim 1 , wherein R 1 , R 2 , R 4 , and R 5 independently are C 2 -C 6 alkyl groups.

3. The polymer of claim 1 , wherein X 1 is a C 10 -C 16 alkyl group or a C 10 -C 16 alkenyl group.

4. The polymer of claim 3 , wherein R 3 is a hydrogen atom and R 1 and R 2 are C 2 alkyl groups.

5. The polymer of claim 3 , wherein R 3 is a bis(aminoalkyl)amide group according to Structure II and R 1 , R 2 , R 4 , and R 5 are C 2 alkyl groups.

6. The polymer of claim 5 , wherein R 1 , R 2 , R 4 , and R 5 are —CH 2 —CH 2 —.

7. The polymer of claim 1 , wherein the monomer having two or more epoxy groups is bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, tetraglycidyl diamine-diphenyl-methane, or a multi-glycidyl ether of phenol formaldehyde novolac polymers.

8. The polymer of claim 7 , wherein the monomer having two or more epoxy groups is bisphenol A diglycidyl ether.

9. The polymer of claim 7 , wherein the monomer having two or more epoxy groups is bisphenol F diglycidyl ether.

Assignees

• Elevance Renewable Sciences

Inventors

• Hunt Zachary
• Christensen S Alexander

Classifications

• C07C231/02 Primary

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

• C08G59/54 Primary

  Amino amides> · 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

• C07C233/38

  having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton · CPC title

• C07C233/36

  having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton · CPC title