Vegetable oil-derived epoxy compositions having improved performance

Patent metadata

Field	Value
Publication number	US-11945905-B2
Application number	US-201917291143-A
Country	US
Kind code	B2
Filing date	Nov 7, 2019
Priority date	Nov 7, 2018
Publication date	Apr 2, 2024
Grant date	Apr 2, 2024

Abstract

Embodiments of this invention are directed to bio-based epoxy compositions, and method of their preparation and use. Other embodiments are directed to cured bio-based epoxies, and manufactured articles having bio-based epoxy coatings, adhesives, or composites.

First claim

What is claimed is:

1. An epoxy composition comprising:
a fatty acid epoxy selected from:

a hyperbranched prepolymer having terminal groups comprising epoxide groups, hydroxyl groups, carboxyl groups, or a combination thereof; and
an aromatic non-coplanar triepoxy.

2. The epoxy composition of claim 1 , wherein the hyperbranched prepolymer has terminal groups consisting of: epoxide groups and hydroxyl groups; epoxide groups and carboxyl groups; or epoxide groups, hydroxyl groups, and carboxyl groups.

3. The epoxy composition of claim 1 , wherein the hyperbranched prepolymer comprises a compound having one of the following structures:

wherein:
X is:

or a combination thereof; and
W is:

or a combination thereof,
wherein

indicates a continued branch of the hyperbranched prepolymer and wherein n1=2 to 12.

4. The epoxy composition of claim 1 , wherein the hyperbranched prepolymer comprises a compound having the structure of Formula (VI):

wherein:
X at each occurrence is independently selected from

W at each occurrence is independently selected from

and
Z is selected from

wherein n1 is 2 to 12, n2 is 2 to 12, and

indicates a continued branch of the hyperbranched prepolymer.

5. The epoxy composition of claim 1 , wherein the aromatic non-coplanar triepoxy is a compound having the structure of Formula (VII):

wherein R 1 and R 2 at each occurrence are independently H, —OCH 3 , or —OCH 2 CH 3 .

6. The epoxy composition of claim 5 , wherein the compound having the structure of Formula (VII) has the following structure:

7. The epoxy composition of claim 1 , wherein the fatty acid epoxy is present at a concentration of about 60% wt. %, the hyperbranched prepolymer is present at a concentration of about 20 wt. %, and the aromatic non-coplanar triepoxy is present at a concentration of about 20 wt. %, based on total weight of the epoxy composition.

8. An epoxy composition comprising a fatty acid epoxy selected from:

and an aromatic non-coplanar triepoxy.

9. The epoxy composition of claim 8 , wherein the aromatic non-coplanar triepoxy is a compound having the structure of Formula (VII):

wherein R 1 and R 2 at each occurrence are independently H, —OCH 3 , or —OCH 2 CH 3 .

10. The epoxy composition of claim 9 , wherein the compound having the structure of Formula (VII) has the following structure:

11. A method of producing a cured epoxy, the method comprising mixing an epoxy composition comprising:
a fatty acid epoxy selected from:

a hyperbranched prepolymer having terminal groups comprising epoxide groups, hydroxyl groups, carboxyl groups, or a combination thereof; and
an aromatic non-coplanar triepoxy,
with a curing agent to produce a curing mixture, and
polymerizing the curing mixture by maintaining the curing mixture at a temperature and time sufficient for polymerizing the epoxy composition, thereby producing a cured epoxy.

12. The method of claim 11 , wherein the curing agent comprises an anhydride curing agent or an amine curing agent.

13. The method of claim 11 , wherein the curing mixture further comprises an accelerator added to the curing mixture at a concentration of about 0.1 wt. % to about 1 wt. %, based on total weight of the curing mixture.

14. The method of claim 11 , wherein the polymerizing is performed between a portion of a surface of a first article and a portion of a surface of a second article, resulting in adhesion of the first article to the second article.

Assignees

• Univ Washington State

Inventors

• Zhang Jinwen
• Liu Tuan

Classifications

• C08G59/12 Primary

  of polycarboxylic acids with epihalohydrins or precursors thereof · CPC title

• C08G59/06

  of polyhydric phenols · CPC title

• C08G59/4238

  heterocyclic · CPC title

• C08G59/502

  Polyalkylene polyamines · CPC title

• C08J5/243

  using carbon fibres · CPC title