# US 8,541,536 B2 · Coupling method for providing high molecular weight natural oil polyol

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- Number: US 8,541,536 B2
- Document ID: US8541536B2
- Status: Granted
- Kind: B2
- Application number: 12/927,086
- Filed: 2010-11-05
- Published: 2011-07-07
- Granted: 2013-09-24
- Earliest claimed: 2010-01-07
- Assignees: MCPU Polymer Engineering, LLC
- Applicants: Thomas M. Garrett; Xian Xian Du
- Inventors: Thomas M. Garrett; Xian Xian Du
- Web page: https://patentgrep.com/patent/US8541536B2

## CPC

- C08G 18/68: Unsaturated polyesters
- C11C 1/04: by hydrolysis
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C11C: FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM

## Abstract

Methods of coupling plant oil based polyols so as to synthesis high molecular weight plant oil polyols having a hydroxyl number between from about 40 to about 60. The resultant polyols may be directly reacted with polyisocyanates to produce polyurethanes.

## Claims

### Claim 1

A process of coupling plant oil based polyols together to produce a plant oil polyol having an increased molecular weight, the process comprising:
a) forming a mixture including a low molecular weight plant oil polyol having a structure according to scheme (I)
and an anhydride coupling reagent; and
b) reacting the mixture at a temperature of from about 100° F. to about 250° F. while simultaneously removing water from the mixture for at least three hours, so as to form a plant oil based product polyol having a structure according to scheme (II)
with a hydroxyl number of between about 50 and 60.

### Claim 2 (depends on 1)

The process of claim 1 wherein:
a) the reaction is performed in the presence of an acid catalyst; and
b) the polyol product is a comparatively high molecular weight polyol and the reaction time for the mixture is in the range from 3-hours to 24-hours.

### Claim 3 (depends on 1)

The process of claim 1 wherein:
a) the reaction is performed in the presence of an acid catalyst; and
b) the coupling reagent is selected from the group consisting of dicarboxylic acid anhydrides, polycarboxylic acid anhydrides, and combinations thereof.

### Claim 4 (depends on 1)

The process of claim 1 wherein:
a) the reaction is performed in the presence of an acid catalyst; and
b) the coupling reagent is selected from the group consisting of diols, triols, quartols, and combinations thereof.

### Claim 5 (depends on 1)

The process of claim 1 wherein:
a) the reaction is performed in the presence of an acid catalyst; and
b) removing water from the mixture includes refluxing the mixture over a Dean-Stark trap.

### Claim 6 (depends on 1)

The process of claim 1 wherein:
a) the reaction is performed in the presence of an acid catalyst; and
b) removing water from the mixture includes reacting the mixture under a vacuum.

### Claim 7 (depends on 1)

The process of claim 1 wherein:
a) the reaction is performed in the presence of an acid catalyst; and
b) the plant oil based polyol is selected from the group consisting of a corn oil polyol, soybean oil polyol, rapeseed oil polyol, sunflower oil polyol, sesame seed oil polyol, peanut oil polyol, safflower oil polyol, olive oil polyol, cotton seed oil polyol, linseed oil polyol, walnut oil polyol, tung oil polyol and combinations thereof.

### Claim 8 (depends on 1)

The process of claim 1 wherein:
a) the reaction is performed in the presence of an acid catalyst; and
b) the plant oil based polyol is a soybean oil polyol having a hydroxyl number of from about 50 to about 60.

### Claim 9 (depends on 1)

A high molecular weight plant oil based polyol with a hydroxyl number of between about 50 and 60 according to claim 1.

### Claim 10 (depends on 9)

The polyol of claim 9, wherein the polyol is a soybean oil based polyol.

### Claim 11 (depends on 1)

A process of preparing a polyurethane comprising the steps of:
a) reacting at least one plant oil based product polyol of claim 1, wherein the plant oil based product polyol includes a hydroxyl number of between about 50 and 60, with an isocyanate.

### Claim 12 (depends on 11)

A polyurethane according to claim 11.