Method of preparing a polycarbodiimide polymer and polycarbodiimide polymer prepared thereby

• US 10,457,767 B2
• Filed: 02/12/2015
• Issued: 10/29/2019
• Est. Priority Date: 02/14/2014
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: Williams-Harry, Michele, Kumar, Rajesh
• Primary Examiner(s): Sergent, Rabon A
• Application Number:
  US15/118,147
• Publication Number:
  US 20170166678A1
• Time in Patent Office: 1,720 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:

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

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:

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.