Method of preparing a polycarbodiimide polymer and polycarbodiimide polymer prepared thereby

Patent metadata

Field	Value
Publication number	US-10457767-B2
Application number	US-201515118147-A
Country	US
Kind code	B2
Filing date	Feb 12, 2015
Priority date	Feb 14, 2014
Publication date	Oct 29, 2019
Grant date	Oct 29, 2019

Abstract

A method of producing a polycarbodiimide polymer comprises heating a precursor compound at a desired temperature. The method further comprises combining the precursor compound, a diisocyanate compound, and a carbodiimidization catalyst to form a reaction mixture. Finally, the method comprises heating the reaction mixture for a first period of time at a first temperature, thereby reacting the precursor compound and the diisocyanate compound in the presence of the carbodiimidization catalyst to produce the polycarbodiimide polymer.

First claim

What is claimed is:

1. A method of producing a polycarbodiimide polymer, said method comprising the steps of:
preparing a precursor compound from a monofunctional isocyanate compound at a desired temperature such that the precursor compound is heated at the desired temperature upon formation;
combining the precursor compound, a diisocyanate compound, and a carbodiimidization catalyst to form a reaction mixture; and
heating the reaction mixture for a first period of time at a first temperature, thereby reacting the precursor compound and the diisocyanate compound in the presence of the carbodiimidization catalyst to produce the polycarbodiimide polymer,
wherein the precursor compound contains a single carbodiimide bond, and
wherein the monofunctional isocyanate is synthesized by reaction of a difunctional isocyanate with a monofunctional alcohol, a monofunctional thiol, or a monofunctional amine.

2. A method as set forth in claim 1 , wherein the monofunctional isocyanate compound is selected from

wherein each R is independently a hydrocarbyl group having from 1 to 20 carbon atoms.

3. A method as set forth in claim 1 , wherein the precursor compound is prepared in the presence of the carbodiimidization catalyst.

4. A method as set forth in claim 1 , wherein said diisocyanate compound comprises an aromatic diisocyanate.

5. A method as set forth in claim 1 , wherein said diisocyanate compound has an ortho-substituted isocyanate group.

6. A method as set forth in claim 1 , wherein said diisocyanate compound comprises toluene diisocyanate.

7. A method as set forth in claim 1 , wherein combining the precursor compound, said diisocyanate compound, and the carbodiimidization catalyst to form the reaction mixture is carried out at the desired temperature.

8. A method as set forth in claim 1 , wherein the desired temperature is from 70 to 150° C.

9. A method as set forth in claim 1 , wherein the first temperature is from 70 to 150° C.

10. A method as set forth in claim 1 , wherein a stabilizing agent is added to the reaction mixture.

11. A method as set forth in claim 10 , wherein the stabilizing agent is selected from triphenylphosphite, 2,6-di-tert-butyl-4-methylphenol, and a combination thereof.

12. A method as set forth in claim 1 , which is carried out in the absence of any solvent other than the precursor compound and said diisocyanate compound.

13. A method as set forth claim 1 , wherein the carbodiimidization catalyst comprises a phospholene compound.

14. A method as set forth in claim 1 , wherein the first period of time is from greater than 0 to 18 hours.

15. A method as set forth in claim 1 , wherein the precursor compound is selected from:

wherein each R is independently a hydrocarbyl group having from 1 to 20 carbon atoms.

16. A method as set forth in claim 1 , wherein the step of preparing the precursor compound is carried out in the absence of said diisocyanate compound.

17. A method as set forth in claim 1 , which is carried out in a single reaction vessel.

Assignees

• Basf Se

Inventors

• Williams-Harry Michele
• Kumar Rajesh

Classifications

• C07C271/28

  to a carbon atom of a non-condensed six-membered aromatic ring · CPC title

• C08G18/16

  Catalysts (catalysts in general B01J) · CPC title

• C08G18/2865

  Compounds having only one primary or secondary amino group; Ammonia · CPC title

• C08G18/3876

  containing mercapto groups · CPC title

• C07C267/00

  Carbodiimides · CPC title