Granted Patent B2

US 7,678,936 · App. 11/842,889 · Granted Mar 16, 2010

Abstract

Claims (41)

1. A method of making an isocyanato terminated precursor for polyurethane, the method comprising:

heating an isocyanate containing about two or more isocyanato groups per molecule at a temperature of up to 80 degrees Celsius and at a pressure of about 1 atmosphere; and

mixing a modified vegetable oil comprising about two or more hydroxyl groups per molecule with the isocyanate at a molar equivalent ratio of at least 2:1 isocyanate to vegetable oil for a predetermined time period to form the isocyanato terminated precursor, wherein the modified vegetable oil comprises a polymerized, oxidized vegetable oil.

2. The method of claim 1 wherein the isocyanate is at least one of 1,1′-methylenebis[isocyanatobenzene], polymethylenepolyphenylene isocyanate, and any isomer or isomer ratio of toluene diisocyanate.

3. The method of claim 1 wherein mixing comprises:

adding the modified vegetable oil comprising hydroxyl groups to the isocyanate;

reacting the modified vegetable oil with the isocyanate to form the isocyanato terminated precursor; and

mixing additional isocyanate with the isocyanate terminated precursor.

4. The method of claim 1 wherein the modified vegetable oil and the isocyanate have temperatures of between about 25 and 70 degrees Celsius.

5. The method of claim 1 further comprising cooling the isocyanato terminated precursor to room temperature.

6. The method of claim 1 wherein mixing reacts the modified vegetable oil with the isocyanate to define the isocyanato terminated precursor in a reaction as follows:

HO—R—OH+(2 +n ){OCN—Ar—CH 2 —[Ar(NCO)—CH 2 ] x —Ar—NCO}------------------>OCN—Ar—CH 2 —[Ar(NCO)—CH 2 ] x —Ar —NHCOO—R—OOCHN—Ar—[CH 2 —Ar(NCO)] x — . . . CH 2 —Ar—NCO+ n {OCN—Ar—CH 2 —[Ar(NCO)—CH 2 ] x —Ar—NCO},

wherein x is greater than or equal to 0 and wherein n is greater than or equal to 0.

7. The method of claim 1 further comprising:

adding up to about 0.002 weight percent phosphoric acid at room temperature; and

adding a catalyst at room temperature.

8. The method of claim 1 further comprising adding up to about 90 weight percent 1,1′-methylenebis[isocyanatobenzene] at room temperature or higher.

9. The method of claim 1 further comprising adding up to about 90 weight percent polymethylenepolyphenylene isocyanate at room temperature or higher.

10. A method of making an isocyanate precursor for polyurethane, the method comprising:

heating an isocyanate containing about two or more isocyanato groups per molecule to a temperature of between about 40 and 70 degrees Celsius at a pressure of about 1 atmosphere; and

adding a modified vegetable oil comprising about two or more hydroxyl groups per molecule and a hydroxyl number of about 52 to the isocyanate at a molar equivalent ratio of at least 2:1 of isocyanate to vegetable oil, the modified vegetable oil having a temperature of between about 25 and 70 degrees Celsius;

mixing the modified vegetable oil with the isocyanate for a predetermined time period to react the modified vegetable oil with the isocyanate to form the isocyanato terminated precursor; and

cooling the isocyanato terminated precursor to room temperature.

11. The method of claim 10 further comprising:

adding up to about 0 to 0.002 weight percent phosphoric acid at room temperature;

adding up to about 90 weight percent

1,1′-methylenebis[isocyanatobenzene] at room temperature or higher; and

adding up to about 90 weight percent polymethylenepolyphenylene isocyanate at room temperature or higher.

12. The method of claim 10 wherein the isocyanate is 1,1′-methylenebis[isocyanatobenzene], polymethylenepolyphenylene isocyanate, and any isomer or isomer ratio of toluene diisocyanate.

13. The method of claim 10 wherein mixing reacts the modified vegetable oil with the isocyanate to define the isocyanato terminated precursor in a reaction as follows:

HO—R—OH+(2 +n ){OCN—Ar—CH 2 —[Ar(NCO)—CH 2 ] x —Ar—NCO}------------------>OCN—Ar—CH 2 —[Ar(NCO)—CH 2 ] x —Ar —NHCOO—R—OOCHN—Ar—[CH 2 —Ar(NCO)] x — . . . CH 2 —Ar—NCO+ n {OCN—Ar—CH 2 —[Ar(NCO)—CH 2 ] x —Ar—NCO},

wherein x is greater than or equal to 0 and wherein n is greater than or equal to 0.

14. The method of claim 10 further comprising adding a catalyst at room temperature.

15. The method of claim 1 wherein prior to the mixing step, the isocyanate is heated to a temperature of between 40 to 70 degrees Celsius at a pressure of about 1 atmosphere, and the modified vegetable oil is heated to a temperature of between 25 and 70 degrees Celsius.

16. The method of claim 10 wherein the mixing step take place after the adding step.

17. The method of claim 10 , wherein the modified vegetable oil comprises a polymerized, oxidized vegetable oil.

18. A method of making an isocyanato terminated precursor for polyurethane, the method comprising:

heating a first amount of isocyanate containing about two or more isocyanato groups per molecule;

mixing a modified vegetable oil comprising about two or more hydroxyl groups per molecule with the isocyanate at a molar equivalent ratio of at least 2:1 isocyanate wherein the modified vegetable oil comprises a polymerized, oxidized vegetable oil;

reacting the modified vegetable oil with the first amount of isocyanate to form an isocyanato terminated precursor; and

mixing a second amount of isocyanate with the isocyanate terminated precursor.

Assignments (14)