Method Of Preparing A Polycarbodiimide Polymer And Polycarbodiimide Polymer Prepared Thereby

• US 20170166678A1
• Filed: 02/12/2015
• Published: 06/15/2017
• Est. Priority Date: 02/14/2014
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: WILLIAMS-HARRY, Michele, KUMAR, Rajesh
• Granted Patent: US 10,457,767 B2
• Time in Patent Office: Days
• CPC Class Codes: C07C 267/00 Carbodiimides
• CPC Class Codes: C07C 271/28 to a carbon atom of a non-condensed six-membered aromatic ring
• CPC Class Codes: C08G 18/025 the polymeric products containing carbodiimide groups
• CPC Class Codes: C08G 18/095 oligomerisation to carbodiimide or uretone-imine groups
• CPC Class Codes: C08G 18/2815 Monohydroxy compounds
• CPC Class Codes: C08G 18/2865 Compounds having only one primary or secondary amino group; Ammonia
• CPC Class Codes: C08G 18/3876 containing mercapto groups
• CPC Class Codes: C08G 18/71 Monoisocyanates or monoisothiocyanates
• CPC Class Codes: C08G 18/76 aromatic
• CPC Class Codes: C08G 18/7621 being toluene diisocyanate including isomer mixtures

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.

Claims

1. A method of producing a polycarbodiimide polymer, said method comprising the steps of:

heating a precursor compound at a desired temperature;

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.

2. A method as set forth in claim 1 further comprising the step of preparing the precursor compound from an initial compound at the desired temperature.

3. A method as set forth in claim 2 wherein the initial compound comprises a monofunctional isocyanate, a monofunctional alcohol, a monofunctional thiol, or a monofunctional amine.

4. A method as set forth in claim 3 wherein the precursor compound comprises a carbodiimide compound, a urethane compound, a thiourethane compound, or a urea compound.

5. A method as set forth in claim 2 wherein the precursor compound is prepared in the presence of the carbodiimidization catalyst.

6. A method as set forth in claim 1 wherein the diisocyanate compound comprises an aromatic diisocyanate.

7. A method as set forth in claim 1 wherein the diisocyanate compound has an ortho-substituted isocyanate group.

8. A method as set forth in claim 1 wherein the diisocyanate compound comprises toluene diisocyanate.

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

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

C.

11. A method as set forth in claim 1 wherein the desired temperature and the first temperature are each independently from 70 to 150°

C.

12. A method as set forth in claim 1 further comprising the step of combining a stabilizing agent with at least the diisocyanate compound and the carbodiimidization catalyst, wherein the stabilizing agent optionally comprises triphenylphosphite or 2,6-di-tert-butyl-4-methylphenol.

13. A method as set forth in claim 1 carried out in the absence of any solvent other than the precursor compound and the diisocyanate compound.

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

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

16. A polycarbodiimide polymer produced in accordance with the method of claim 1.

17. A method as set forth in claim 2 wherein the initial compound comprises a monofunctional isocyanate.

18. A method as set forth in claim 1 wherein the precursor compound has the following general formula:

R—

N═

C═

N—

R

wherein each R is an aromatic group.

19. A method as set forth in claim 1 wherein the step of heating the precursor compound at the desired temperature is carried out in the absence of the diisocyanate compound.

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