Preparation of vegetable oil-based monomers for use in thermosetting resins

Patent metadata

Field	Value
Publication number	US-10513484-B2
Application number	US-201715697957-A
Country	US
Kind code	B2
Filing date	Sep 7, 2017
Priority date	Sep 8, 2016
Publication date	Dec 24, 2019
Grant date	Dec 24, 2019

Abstract

The present embodiments herein generally relate to thermoset resins that are derived from vegetable oil based sources, including fibrous plant sources. The utilization of plant based oil as starting materials makes the technology a green alternative to currently available solutions. This, coupled with the novel synthetic methods that are utilized, results in a transformation of the plant based oils into useful, durable, and resilient thermoset resins.

First claim

What is claimed is:

1. A fatty acid-derived compound having the Formula I:

wherein,
R 1 , R 2 , R 3 , and R 4 are independently hydrogen, an acrylate group, or a methacrylate group

wherein R 6 is hydrogen or a methyl group;
R 5 is a methacrylate group

or an organosilane group with structure

R 7 is a methyl or an ethyl group;
R 8 is a vinyl or an acrylate group

and L 1 is independently C 1 -C 9 alkylene or C 1 -C 9 alkenylene.

2. The compound of claim 1 , wherein the compound is:

3. The compound of claim 1 , wherein the compound is:

wherein R is hydrogen or a methyl group.

4. The compound of claim 1 , wherein R 3 is an acrylate or a methacrylate group.

5. The compound of claim 1 , wherein R 3 is an acrylate group.

6. The compound of claim 1 , wherein R 4 is an acrylate or a methacrylate group.

7. The compound of claim 1 , wherein R 4 is an acrylate group.

8. The compound of claim 1 , wherein R 1 is H.

9. The compound of claim 1 , wherein R 2 is H.

10. The compound of claim 1 , wherein L 1 is C 1 -C 9 alkylene.

11. The compound of claim 10 , wherein L 1 is C 5 alkylene.

12. The compound of claim 1 , wherein L 1 is C 1 -C 9 alkenylene.

13. The compound of claim 12 , wherein L 1 is C 5 alkenylene.

14. A compound having the following structure:

15. A composition comprising a first fatty acid-derived compound having the Formula I:

wherein
R 1 , R 2 , R 3 and R 4 are independently hydrogen, an acrylate group, or a methacrylate group

wherein R 6 is hydrogen or a methyl group;
R 5 is a methacrylate group

or an organosilane group with structure

R 7 is a methyl or an ethyl group;
R 8 is a vinyl or an acrylate group

 and
L 1 is independently C 1 -C 9 alkylene or C 1 -C 9 alkenylene, and a second fatty acid-derived compound.

16. The composition of claim 15 , wherein R 3 is an acrylate group.

17. The composition of claim 15 , wherein R 4 is an acrylate group.

18. The composition of claim 15 , wherein R 1 and R 2 are both H.

19. The composition of claim 15 , wherein the first fatty acid-derived compound is:

20. The composition of claim 15 , wherein the first fatty acid-derived compound is:

wherein R is hydrogen or methyl group.

Assignees

• Univ Washington State

Inventors

• Zhang Jinwen
• Xin Junna

Classifications

• C07F7/04

  Esters of silicic acids · CPC title

• C08K5/10

  Esters; Ether-esters · CPC title

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• C07C69/67 Primary

  of saturated acids · CPC title

• C07C323/52

  the carbon skeleton being acyclic and saturated · CPC title