IP Library › Granted Patent US 10,882,950
Granted Patent B2
US 10,882,950 · App. 16/457,352 · Granted Jan 5, 2021

Curative

Inventors: Aaron Kenneth Amstutz (Peoria, IL); Luke Michael Haverhals (Peoria, IL); Albert C Pierz (Peoria, IL); Ian T Pierz (Peoria, IL)
Assignee: Natural Fiber Welding, Inc.
C08G63/42B32B5/022B32B5/024B32B9/06B32B25/10B32B25/12C08C19/06C08G63/81C08J3/24B32B2305/72B32B2307/50B32B2319/00C08J2315/00
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Quick Facts
Patent No.
US 10,882,950
App. No.
16/457,352
Granted
Jan 5, 2021
Kind
B2
Abstract

A curative for epoxidized plant-based oils and epoxidized natural rubber is created from the reaction between a naturally occurring polyfunctional acid and an epoxidized plant-based oil is disclosed. The curative may be used to produce porosity-free castable resins and vulcanize rubber formulations based on epoxidized natural rubber. Materials made from disclosed materials may be advantageously used as leather substitutes.

Claims (32)

1. A method of preparing a curative, said method comprising the steps of:

a. dissolving a polyfunctional carboxylic acid in a hydroxyl-containing solvent to create a first mixture;

b. adding an epoxidized triglyceride to said first mixture to create a second mixture;

c. heating said second mixture to a temperature near a boiling point of said hydroxyl-containing solvent;

d. allowing said polyfunctional carboxylic acid to react with said epoxidized triglyceride;

e. allowing said hydroxyl-containing solvent to form an ester linkage between said hydroxyl-containing solvent and said naturally occurring polyfunctional carboxylic acid;

f. removing an unreacted portion of said hydroxyl-containing solvent.

2. The method according to claim 1 wherein said step of allowing said polyfunctional carboxylic acid to react with said epoxidized triglyceride and said step of allowing said hydroxyl-containing solvent to form an ester linkage between said hydroxyl-containing solvent and said naturally occurring polyfunctional carboxylic acid are further defined as occurring concurrently.

3. The method according to claim 1 wherein said hydroxyl-containing solvent is further defined as being combined with a non-hydroxyl-containing solvent.

4. The method according to claim 3 wherein said non-hydroxyl-containing solvent is further defined as acetone.

5. An epoxidized natural rubber-based material comprising a mixture of a curative and an epoxidized natural rubber, said curative comprising a reaction product among a naturally occurring polyfunctional carboxylic acid, a hydroxyl-containing solvent, and an epoxidized triglyceride, wherein said curative includes a formed ester linkage between said hydroxyl-containing solvent and said naturally occurring polyfunctional carboxylic acid.

6. The epoxidized natural rubber-based material according to claim 5 wherein said naturally occurring polyfunctional carboxylic acid is further defined as being selected from a group consisting of citric acid, tartaric acid, succinic acid, malic acid, maleic acid, and fumaric acid.

7. The epoxidized natural rubber-based material according to claim 5 wherein said epoxidized triglyceride is further defined as being selected from a group consisting of epoxidized soybean oil, epoxidized linseed oil, epoxidized corn oil, epoxidized cottonseed oil, epoxidized canola oil, epoxidized rapeseed oil, epoxidized grape seed oil, epoxidized poppy seed oil, epoxidized tongue oil, epoxidized sunflower oil, epoxidized safflower oil, epoxidized wheat germ oil, epoxidized walnut oil, and epoxidized microbial-produced oil.

8. The epoxidized natural rubber-based material according to claim 7 wherein said epoxidized natural rubber is further defined as having a level of epoxidation between 3% and 50%.

9. An article generally configured as a sheet, said article comprising:

a. a first layer of an epoxidized natural rubber-based material comprising a mixture of a curative and an epoxidized natural rubber, said curative comprising a reaction product among a naturally occurring polyfunctional carboxylic acid, a hydroxyl-containing solvent, and an epoxidized triglyceride, wherein said curative includes a formed ester linkage between said hydroxyl-containing solvent and said naturally occurring polyfunctional carboxylic acid; and,

b. a backing material positioned adjacent said first layer.

10. The article according to claim 9 wherein an area of said backing material is less than an area of said first layer and wherein a thickness of a first end of said sheet is greater than a thickness of a second end of said sheet.

11. The article according to claim 9 wherein an area of said first layer is further defined as being formed with a surface feature thereon.

12. The article according to claim 9 further comprising a second backing material positioned adjacent said backing material.

13. The article according to claim 9 further comprising a second layer of an epoxidized natural rubber-based material comprising a mixture of a curative and an epoxidized natural rubber, said curative comprising a reaction product among a naturally occurring polyfunctional carboxylic acid, a hydroxyl-containing solvent, and an epoxidized triglyceride, wherein said curative includes a formed ester linkage between said hydroxyl-containing solvent and said naturally occurring polyfunctional carboxylic acid, and wherein said second layer is positioned adjacent said backing material.

14. The article according to claim 12 further comprising a second layer of an epoxidized natural rubber-based material comprising a mixture of a curative and an epoxidized natural rubber, said curative comprising a reaction product among a naturally occurring polyfunctional carboxylic acid, a hydroxyl-containing solvent, and an epoxidized triglyceride, wherein said curative includes a formed ester linkage between said hydroxyl-containing solvent and said naturally occurring polyfunctional carboxylic acid, and wherein said second layer is positioned adjacent said second backing material.

15. The article according to claim 12 wherein said second backing material is further defined as comprising:

a. a resin comprising a mixture of a pre-polymer and an epoxidized triglyceride, said pre-polymer comprising a reaction product among a naturally occurring polyfunctional carboxylic acid, a hydroxyl-containing solvent, and a second epoxidized triglyceride, wherein said curative includes a formed ester linkage between said hydroxyl-containing solvent and said naturally occurring polyfunctional carboxylic acid; and,

b. a backing layer, wherein said resin impregnates a portion of said backing layer.

16. The article according to claim 15 wherein said first layer of an epoxidized natural rubber-based material is further defined as having a texture thereon.

17. The article according to claim 16 wherein said texture is further defined as matching a texture paper.

18. The article according to claim 15 wherein said second layer an epoxidized natural rubber-based material is further defined as having a second texture thereon.

19. The article according to claim 18 wherein said second texture is further defined as matching a second texture paper.

20. The article according to claim 15 wherein said backing layer is further defined as a non-woven textile.

21. The article according to claim 15 wherein said backing layer is further defined as a woven textile.

22. The article according to claim 15 wherein said backing layer is further defined as comprising a natural fiber.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 24, 2021
From: NATURAL FIBER WELDING, INC.
To: NATURAL FIBER WELDING, INC.
Reel/Frame 055708/0768 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 2, 2019
From: AMSTUTZ, AARON KENNETH; HAVERHALS, LUKE; PIERZ, ALBERT C; PIERZ, IAN T
To: NATURAL FIBER WELDING, INC.
Reel/Frame 049654/0810 →
Continuity (9)
Continuation 16388693 · Apr 18, 2019
Provisional Application 62806480 · Feb 15, 2019
Provisional Application 62772715 · Nov 29, 2018
Provisional Application 62772744 · Nov 29, 2018
Provisional Application 62756062 · Nov 5, 2018
Provisional Application 62669483 · May 10, 2018
Provisional Application 62669502 · May 10, 2018
Provisional Application 62660943 · Apr 21, 2018
Related Publication 20190322799A1 · Oct 24, 2019
Cited By (2)
US 12,247,098 US 12,344,706