US2010160593A1PendingUtilityA1

Isocyanato terminated precursor and method of making the same

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Assignee: LEAR CORPPriority: Aug 21, 2007Filed: Mar 9, 2010Published: Jun 24, 2010
Est. expiryAug 21, 2027(~1.1 yrs left)· nominal 20-yr term from priority
Inventors:Thomas N. JonesEdmund J. Madaj
C08G 18/36C08G 2101/00C08G 18/7671
49
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Claims

Abstract

A method of making an isocyanato terminated precursor for polyurethane is disclosed. The method comprises 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. The method further comprises 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.

Claims

exact text as granted — not AI-modified
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.

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