ISOCYANATO TERMINATED PRECURSOR AND METHOD OF MAKING THE SAME

1 . A method of making a polyurethane product from an isocyanato terminated precursor, the method comprising:

heating an isocyanate containing about two or more isocyanato groups per molecule to a temperature of between about 25 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 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, the modified vegetable oil comprising a polymerized, oxidized vegetable oil;

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;

providing a polyol mixture (B-side reactants) comprising a base polyol, a catalyst and an additive;

mixing the polyol mixture (B-side reactants) in a weight ratio with the isocyanato terminated precursor (A-side reactants) so that the active hydrogen content of the polyol mixture (B-side reactants) in equivalent units is between about 80:100 and 100:60 to the isocyanato equivalent units in the isocyanate precursor (A-side reactants), the polyol mixture (B-side reactants) are mixed with the isocyanato precursor (A-side reactants) at a predetermined pressure and a temperature of between about 20 and 50 degrees Celsius, defining a liquid polyurethane mixture; and

reacting the polyurethane mixture in situ to form the polyurethane product.

2 . The method of claim 1 further comprising:

cooling the isocyanato terminated precursor to room temperature; and

reacting in situ the polyurethane mixture for a defined period of time in a mold of a predetermined shape to form the polyurethane product.

3 . The method of claim 1 wherein mixing the modified vegetable comprises:

adding up to about 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.

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

5 . The method of claim 1 wherein mixing the modified vegetable oil with the isocyanate reacts the modified vegetable oil with the isocyanate, defining the isocyanato terminated precursor 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.

6 . The method of claim 1 wherein the predetermined pressure when mixing B-side reactants with A-side reactants is up to about 2 atmospheres.

7 . The method of claim 1 wherein the predetermined pressure when mixing B-side reactants with A-side reactants is between about 1500 and 3000 pounds per square inch gauge.

8 . 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.

9 . The method of claim 1 wherein mixing the modified vegetable oil with the isocyanate 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.

10 . The method of claim 1 wherein reacting the modified vegetable oil with the isocyanate defines 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.

11 . A method of making a polyurethane product from an isocyanato terminated precursor, the method comprising:

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

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

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;

providing a polyol mixture (B-side reactants) comprising base polyol and catalyst;

mixing the polyol mixture (B-side reactants) in a weight ratio with the isocyanato terminated precursor (A-side reactants) so that the active hydrogen content of the polyol mixture (B-side reactants) in equivalent units is between about 80:100 and 100:60 to the isocyanato equivalent units in the isocyanate precursor (A-side reactants), mixture to define a liquid polyurethane mixture; and

reacting the polyurethane mixture in situ to form the polyurethane product.

12 . The method of claim 11 wherein the modified vegetable oil has a temperature of between about 25 and 70 degrees Celsius.

13 . The method of claim 11 wherein the temperature of the isocyanate is between about 25 and 70 degrees Celsius.

14 . The method of claim 11 further comprising:

cooling the isocyanato terminated precursor to room temperature; and

reacting in situ the polyurethane mixture for a defined period of time in a mold of a predetermined shape to form the polyurethane product.

15 . The method of claim 14 wherein mixing the modified vegetable comprises:

adding up to about 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.

16 . The method of claim 11 wherein the isocyanate is 1,1′-methylenebis[isocyanatobenzene], polymethylenepolyphenylene isocyanate, and any isomer or isomer ratio of toluene diisocyanate.

17 . The method of claim 11 wherein mixing the modified vegetable oil with the isocyanate reacts the modified vegetable oil with the isocyanate, defining the isocyanato terminated precursor 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.

18 . The method of claim 11 wherein the isocyanate is at least one of 1,1′-methylenebis[isocyanatobenzene], polymethylenepolyphenylene isocyanate, and any isomer or isomer ratio of toluene diisocyanate.

19 . A method of making a polyurethane product from an isocyanato terminated precursor, the method comprising:

heating an isocyanate containing about two or more isocyanato groups per molecule to a temperature of between about 25 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 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;

providing a polymeric mixture (B-side reactants) comprising a base polyol and a catalyst;

mixing the polyol mixture (B-side reactants) with the isocyanato terminated precursor (A-side reactants) define a liquid polyurethane mixture; and

reacting the polyurethane mixture in situ to form the polyurethane product.

20 . The method of claim 19 wherein the modified vegetable oil comprising a polymerized, oxidized, vegetable oil.