Process for isocyanate modification using spirocyclic ammonium salts as catalyst

Patent metadata

Field	Value
Publication number	US-9850338-B2
Application number	US-201515119177-A
Country	US
Kind code	B2
Filing date	Feb 13, 2015
Priority date	Feb 18, 2014
Publication date	Dec 26, 2017
Grant date	Dec 26, 2017

Abstract

The Invention relates to a process for modifying isocyanates, in which at least one monomeric organic isocyanate having an NCO functionality>1 is oligomerized in the presence of at least one spirocyclic ammonium salt having a cation of the formula I as catalysts for the isocyanate modification, where substituents X and Y in the N positions are identical or different, substituted or unsubstituted C2-C20-alkylene chains optionally interrupted by heteroatoms (O, N, S) and by aromatic rings. The invention further relates to the use of such a catalyst.

First claim

The invention claimed is:

1. A process for modifying isocyanates comprising:
oligomerizing at least one monomeric organic isocyanate having an NCO functionality >1 in the presence of at least one catalyst comprising at least one spirocyclic ammonium salt having a cation of the formula I

wherein the nitrogen substituents X and Y are independently identical or different, substituted or unsubstituted C2-C20-alkylene chains, optionally interrupted by heteroatoms (O, N, S) and aromatic rings.

2. The process according to claim 1 , wherein X and/or Y are each independently optionally substituted C4-C6-alkylene chains.

3. The process according to claim 1 , wherein an anion of the at least one spirocyclic ammonium salt is selected from the group consisting of hydroxide, alkanoate, carboxylate, heterocycles having at least one negatively charged nitrogen atom in the ring.

4. The process according to claim 1 , wherein the oligomerization is conducted in the presence of a solvent and/or an additive.

5. The process according to claim 1 , wherein the monomeric organic isocyanate is selected from aliphatic diisocyanates.

6. The process according to claim 1 wherein the catalyst of the formula I is used in an amount of 0.001 to 5 mol %, based on the sum total of the molar amounts of the monomeric organic isocyanate used and the catalyst.

7. The process according to claim 1 , wherein the process is conducted within the temperature range from 0° C. to +250° C.

8. The process according to claim 1 , wherein the oligomerization is stopped after 5% to 80% by weight of the monomeric organic isocyanate has been converted.

9. The process according to claim 8 , wherein the oligomerization is stopped by deactivating the catalyst.

10. The process according to claim 8 , wherein unconverted monomeric organic isocyanate is separated from the reaction mixture.

11. The process according to claim 2 , wherein the C4-C6-alkylene chains are linear in structure.

12. The process according to claim 3 , wherein the anion is selected from the group consisting of azolate, imidazolate, triazolate or tetrazolate, fluoride, hydrogendifluoride and mixtures of these.

13. The process according to claim 5 , wherein the monomeric organic isocyanate is selected from the group consisting of hexamethylene diisocyanate (HDI), 2-methylpentane 1,5-diisocyanate, 2,4,4-trimethylhexane 1,6-diisocyanate, 2,2,4-trimethylhexane 1,6-diisocyanate, 4-isocyanatomethyloctane 1,8-diisocyanate, 3(4) -isocyanatomethyl- 1-methylcyclohexyl isocyanate (IMCI), isophorone diisocyanate (IPDI), 1,3- and 1,4-bis(isocyanatomethyl)benzene (XDI), 1,3- and 1,4-bis(isocyanato -methyl)cyclohexane (H6XDI) and mixtures of these.

14. The process according to claim 6 , wherein the catalyst of the formula I is used in an amount of 0.002 to 2 mol% of catalyst.

15. The process according to claim 7 , wherein the process is conducted within the temperature range from 20 to 180° C.

16. The process according to claim 7 , wherein the process is conducted within the temperature range from 40 to 150° C.

17. The process according to claim 8 , wherein the process is stopped after 10% to 60% by weight of the monomeric organic isocyanate has been converted.

18. The process according to claim 9 , wherein the step of deactivating the catalyst comprises adding an acid or an acid derivative, adsorptively binding the catalyst and then removing the catalyst by filtration.

Assignees

• Covestro Deutschland Ag

Inventors

• Richter Frank

Classifications

• C08G18/027

  the polymeric products containing urethodione groups · CPC title

• C08G18/2081 Primary

  containing at least two non-condensed heterocyclic rings · CPC title

• C08G18/022 Primary

  the polymeric products containing isocyanurate groups · CPC title

• C08G18/02

  of isocyanates or isothiocyanates only · CPC title

• C08G2105/02

  Chemistry & Metallurgy · mapped topic