IP Library Granted Patent US 11,993,733
Granted Patent B2
US 11,993,733 · App. 17/204,475 · Granted May 28, 2024

Bio-based coatings and adhesives using oils of

Inventors: Greg Curtzwiler (Boone, IA); Keith Vorst (Madrid, IA); Alexandra Ivey (Ames, IA); Sharan Raman (Wheaton, IL)
Assignee: IOWA STATE UNIVERSITY RESEARCH FOUNDATION, INC.
C09J175/14C08G18/3218C08G18/4277C08G18/675C08G18/728C08G18/73C08G63/52C08G63/81C09J5/00C09J11/04C09J167/08C09J2467/00C09J2475/00
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Quick Facts
Patent No.
US 11,993,733
App. No.
17/204,475
Granted
May 28, 2024
Kind
B2
Abstract

The present application relates to polyurethane polymers produced by polymerizing a reactant mixture comprising triglycerides of Physaria fendleri , one or more polyisocyanates, and one or more polyols, wherein the triglycerides of Physaria fendleri have a hydroxyl value ranging from 90 milligrams of potassium hydroxide per gram of the triglycerides of Physaria fendleri to 250 milligrams of potassium hydroxide per gram of the triglycerides of Physaria fendleri . The present application also relates to polyester polymers produced by polymerizing a reactant mixture comprising triglycerides of Euphorbia Lagascae , and one or more dicarboxylic acids. Also disclosed are the methods of formation of the polyurethane and polyester polymers, and their use as adhesives.

Claims (29)

1. A polyurethane polymer produced by polymerizing a reactant mixture comprising:

triglycerides of unmodified Physaria fendleri;

one or more polyisocyanates;

one or more polyols; and

a polymer formed from triglycerides of Euphorbia Lagascae and one or more dicarboxylic acids, wherein the triglycerides of unmodified Physaria fendleri have a hydroxyl value ranging from 90 milligrams of potassium hydroxide per gram of the triglycerides of unmodified Physaria fendleri to 250 milligrams of potassium hydroxide per gram of the triglycerides of unmodified Physaria fendleri.

2. The polymer of claim 1 , wherein the reactant mixture further comprises:

triglycerides of castor oil.

3. The polymer of claim 1 , wherein the reactant mixture further comprises:

triglycerides with at least two naturally containing hydroxyl functional fatty acids.

4. The polymer of claim 1 , wherein the polyol is selected from the group consisting of polycaprolactone diol, poly(tetrahydrofuran), isosorbide, ethylene glycol, polyethylene glycol, propylene glycol, butylene glycol, polyethylene oxide, glycerol, and sugar alcohols.

5. The polymer of claim 1 , wherein the polyurethane polymer comprises triglycerides of unmodified Physaria fendleri to polyol in a molar ratio ranging from 4.5:1 to 0.01:1.

6. The polymer of claim 1 , wherein the polyisocyanate is selected from the group consisting of hexamethylene diisocyanate, poly(hexamethylene diisocyanate), dicyclohexylmethane 4,4′-diisocyanate, isophorone diisocyanate, 4,4′-diphenylmethane diisocyanate, toluene diisocyanate, ethylene diisocyanate, and paraphenyl diisocyanate.

7. The polymer of claim 1 , wherein the polyurethane polymer comprises triglycerides of unmodified Physaria fendleri to the polyisocyanate in a molar ratio ranging from 1:0.5 to 1:1.5.

8. The polymer of claim 1 , wherein the polyurethane polymer has a number average molecular weight ranging from 3000 grams per mole of the polyurethane polymer to 1,000,000 grams per mole of the polyurethane polymer.

9. The polymer of claim 1 , wherein the polyurethane polymer has a glass transition point ranging from −50° C. to 110° C.

10. An adhesive composition comprising:

the polymer of claim 1 and

a solvent.

11. The adhesive composition according to claim 10 further comprising:

a tackifier and/or a plasticizer.

12. The adhesive composition according to claim 10 further comprising:

a filler selected from the group consisting of ground mica, talc, kaolin clay, calcium carbonate, calcium sulfite, colloidal silica, wollastonite, ballotini, hollow glass microspheres, glass, carbon and graphite fibers, zinc, titanium, zirconium, ground quartz, metallic silicates, and metallic powders.

13. A method of adhering substrates together, said method comprising:

providing a plurality of substrates;

applying the polymer of claim 1 to one or more of the substrates; and

joining the substrates together with the applied polymer.

14. The polymer of claim 1 , wherein the polymer is a linear polymer.

15. The polymer of claim 1 , wherein the contact angle of the polymer is between 70° and 100°.

16. The polymer of claim 1 , wherein the polymer comprises a 1:1 equivalence ratio of Physaria fendleri to polyisocyanate.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 30, 2021
From: CURTZWILER, GREG; VORST, KEITH; IVEY, ALEXANDRA; RAMAN, SHARAN
To: IOWA STATE UNIVERSITY RESEARCH FOUNDATION, INC.
Reel/Frame 055762/0756 →
Continuity (2)
Provisional Application 62991167 · Mar 18, 2020
Related Publication 20210292623A1 · Sep 23, 2021