IP Library Granted Patent US 11,453,777
Granted Patent B2
US 11,453,777 · App. 16/469,560 · Granted Sep 27, 2022

Pressure sensitive adhesives from plant oil-based polyols

Inventors: Jian Huang (Corvallis, OR); Anlong Li (Corvallis, OR); Kaichang Li (Corvallis, OR)
Assignee: Oregon State University
C08L75/08C08G18/4845C08G18/7621C08L91/00C09J7/38
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Quick Facts
Patent No.
US 11,453,777
App. No.
16/469,560
Granted
Sep 27, 2022
Kind
B2
Abstract

A polymer made by: (A) initially reacting poly(propylene glycol) with tolylene diisocyanate to form an intermediate product, and (B) subsequently reacting the resulting intermediate product with at least one polyol, wherein the polyol was derived from, or is, a plant oil.

Claims (32)

1. A polymer made by:

(A) initially reacting poly(propylene glycol) with tolylene diisocyanate to form an intermediate product, and

(B) subsequently reacting the resulting intermediate product with at least one polyol, wherein the polyol was derived from, or is, soybean oil.

2. The polymer of claim 1 , wherein the poly(propylene glycol) has a number-average molecular weight of 300 to 4000.

3. The polymer of claim 1 , wherein the poly(propylene glycol) is reacted with the tolylene diisocyanate at a temperature below 80° C.

4. The polymer of claim 1 , wherein the polyol has a hydroxyl functionality of 2 to 6.

5. The polymer of claim 1 , wherein a reaction mixture of the intermediate product and the at least one polyol is initially heated until conversion of NCO groups in the intermediate product reaches a degree ranging from 30% to 95%, and then subsequently cured at room temperature.

6. The polymer of claim 1 , wherein the poly(propylene glycol), the tolylene diisocyanate, and the at least one polyol are the only reactive starting materials.

7. The polymer of claim 1 , wherein the tolylene diisocyanate is tolylene-2,4-diisocyanate, tolylene-2,6-diisocyanate or a mixture of tolylene-2,4-diisocyanate and tolylene-2,6-diisocyanate.

8. A polymer made by reacting tolylene 2,4-diisocyanate terminated poly(propylene glycol) with at least one polyol, wherein the polyol was derived from, or is, soybean oil.

9. A polyurethane comprising a poly(propylene glycol) repeating unit, a tolylene diisocyanate repeating unit, and a polyol repeating unit, wherein the polyol was derived from soybean oil.

10. A polyurethane having a structure represented by:

wherein PPG denotes a monomeric unit from poly(propylene glycol); the polyol was derived from a plant oil; m is 1 to 100; and n is 1 to 100.

11. A pressure sensitive adhesive construct comprising:

(A) a backing substrate; and

(B) a pressure sensitive adhesive disposed on the backing substrate, wherein the pressure sensitive adhesive comprises a polymer made by:

(i) initially reacting poly(propylene glycol) with tolylene diisocyanate to form an intermediate product, and

(ii) subsequently reacting the resulting intermediate product with at least one polyol, wherein the polyol was derived from, or is, a plant oil.

12. A pressure sensitive adhesive construct comprising:

(A) a backing substrate; and

(B) a pressure sensitive adhesive disposed on the backing substrate, wherein the pressure sensitive adhesive comprises the polyurethane of claim 9 .

13. A method for making a pressure sensitive adhesive comprising:

(A) initially reacting poly(propylene glycol) with tolylene diisocyanate to form an intermediate product, and

(B) subsequently reacting the resulting intermediate product with at least one polyol, wherein the polyol was derived from, or is, a plant oil.

14. A method for making a pressure sensitive adhesive comprising reacting tolylene 2,4-diisocyanate terminated poly(propylene glycol) with at least one polyol, wherein the polyol was derived from, or is, a plant oil.

15. The method of claim 13 , wherein the polyol was derived from soybean oil.

16. The method of claim 13 , wherein the polyol is castor oil.

17. The method of claim 13 , wherein the poly(propylene glycol) has a number-average molecular weight of 300 to 4000.

18. The method of claim 13 , wherein the poly(propylene glycol) is reacted with the tolylene diisocyanate at a temperature below 80° C.

19. The method of claim 13 , wherein the polyol has a hydroxyl functionality of 2 to 6.

20. The method of claim 13 , wherein a mixture of the intermediate product and the at least one polyol is initially heated until the conversion of NCO groups in the intermediate product reaches a degree ranging from 30% to 95%, and then subsequently cured at room temperature.

21. The method of claim 13 , wherein the poly(propylene glycol), the tolylene diisocyanate, and the at least one polyol are the only reactive starting materials.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 20, 2019
From: HUANG, JIAN; LI, ANLONG; LI, KAICHANG
To: OREGON STATE UNIVERSITY
Reel/Frame 049544/0366 →
Continuity (2)
Provisional Application 62435594 · Dec 16, 2016
Related Publication 20200079957A1 · Mar 12, 2020