IP Library Granted Patent US 8,471,072
Granted Patent B2
US 8,471,072 · App. 12/698,652 · Granted Jun 25, 2013

Soy-based polyols

Inventors: Galen Suppes (Columbia, MO); Zuleica Lozada (Columbia, MO); Arnold Lubguban (Columbia, MO)
Assignee: The Curators of the University of Missouri
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Quick Facts
Patent No.
US 8,471,072
App. No.
12/698,652
Granted
Jun 25, 2013
Kind
B2
Abstract

The invention provides processes for preparing soy-based oligomeric polyols or substituted oligomeric polyols, as well as urethane bioelasteromers comprising the oligomeric polyols or substituted oligomeric polyols.

Claims (10)

1. A process for preparing an oligomeric polyol, the process comprising contacting an epoxidized triglyceride having a viscosity of about 3,000 to about 6,000 cP at 22° C. with a hydroxyl-containing reactant in the presence of an aromatic sulfonic acid to form the oligomeric polymer, the oligomeric polymer having a hydroxyl value of at least 100 mg KOH/g.

2. The process of claim 1 , wherein the epoxidized triglyceride is derived from soybean oil, and wherein about 20% to 100% of the double bonds of the epoxidized triglyceride comprise an oxirane ring.

3. The process of claim 2 , wherein about 60% to 90% of the double bonds of the epoxidized triglyceride comprise an oxirane ring.

4. The process of claim 2 , wherein epoxidized triglyceride has an epoxy content of about 5% to about 6.5%.

5. The process of claim 1 , wherein the epoxidized triglyceride has a viscosity of about 3,500 to about 4,500 cP at 22° C.

6. The process of claim 1 , wherein the hydroxyl-containing reactant is chosen from an alcohol and a diacid.

7. The process of claim 6 , wherein the alcohol is a diol chosen from ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and tetraethylene glycol.

8. The process of claim 1 , wherein the aromatic sulfonic acid is chosen from p-toluenesulfonic acid and benzenesulfonic acid.

9. The process of claim 1 , wherein the molar ratio of the epoxidized triglyceride to the hydroxyl-containing reagent to the aromatic sulfonic acid is about 1:0.1:0.005 to about 1:3:0.2; and the process is conducted at a temperature of about 100° C. to about 240° C.

10. The process of claim 1 , wherein the hydroxyl-containing reactant is ethylene glycol; the aromatic sulfonic acid is p-toluenesulfonic acid; the molar ratio of epoxidized triglyceride to ethylene glycol to p-toluenesulfonic acid is about 1:0.4:0.02 to about 1:0.8:0.05; and the process is conducted at a temperature of about 130° C. to about 160° C.

Assignments (2)
CONFIRMATORY LICENSE Recorded Jul 11, 2013
From: UNIVERSITY OF MISSOURI, COLUMBIA
To: ENERGY, UNITED STATES DEPARTMENT OF
Reel/Frame 030822/0331 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 23, 2010
From: SUPPES, GALEN; LOZADA, ZULEICA; LUBGUBAN, ARNOLD
To: THE CURATORS OF THE UNIVERSITY OF MISSOURI
Reel/Frame 024125/0512 →
Continuity (5)
Continuation In Part 11746445 · May 9, 2007
Provisional Application 60799061 · May 9, 2006
Provisional Application 60857438 · Nov 7, 2006
Provisional Application 61206717 · Feb 2, 2009
Related Publication 20100190951A1 · Jul 29, 2010