Use of succinonitrile in the production of polyisocyanates comprising iminooxadiazinedione groups

Patent metadata

Field	Value
Publication number	US-9938369-B2
Application number	US-201414905853-A
Country	US
Kind code	B2
Filing date	Jul 21, 2014
Priority date	Jul 25, 2013
Publication date	Apr 10, 2018
Grant date	Apr 10, 2018

Abstract

The present invention relates to a method for producing polyisocyanates comprising iminooxadiazinedione groups, wherein at least one monomeric di- and/or tri-isocyanate is oligomerized in the presence of at least one catalyst and succinonitrile. The invention relates further to a reaction system for producing polyisocyanates comprising iminooxadiazinedione groups, and to the use of succinonitrile in the production of polyisocyanates comprising iminooxadiazinedione groups by catalyzed modification of monomeric di- and/or tri-isocyanates.

First claim

The invention claimed is:

1. A method for producing polyisocyanates containing iminooxadiazinedione groups, wherein the method comprises oligomerizing at least one monomeric di- and/or tri-isocyanate in the presence of at least one catalyst and succinonitrile, wherein the catalyst is a tetraorganyl-ammonium salt or a tetraorganyl-phosphonium salt, wherein the anions of the tetraorganyl-ammonium salt or tetraorganyl-phosphonium salt are selected from the group: RfCR 1 R 2 COO − , wherein Rf represents a straight-chained or branched perfluoroalkyl radical and R 1 and R 2 independently represent H, straight-chained or branched organyl radicals, fluoride (F − ), di- and/or poly-(hydrogen) fluorides ([F − ×HF) m ]), and wherein m has a numerical value of from 0.001 to 20.

2. The method according to claim 1 , wherein the amount of succinonitrile is from 0.001 to 30%, based on the monomeric di- and/or tri-isocyanate.

3. The method according to claim 1 wherein the monomeric di- and/or tri-isocyanate comprises an aliphatic diisocyanate.

4. The method according to claim 1 , wherein the di- and/or poly-(hydrogen) fluoride ([F − ×HF) m ]) is selected from the group consisting of a quaternary ammonium fluoride, ammonium difluoride, ammonium trifluoride, an ammonium polyfluoride, a phosphonium fluoride, a phosphonium difluoride, a phosphonium trifluoride and/or a phosphonium polyfluoride.

5. The method according to claim 1 , wherein the catalyst is used in an amount of from 1 mol-ppm to 1 mol-%, based on the amount of monomeric di- and/or tri-isocyanate.

6. The method according to claim 1 , wherein the method is carried out in the temperature range of from 0° C. to +250° C.

7. The method according to claim 1 , wherein the oligomerization is terminated when from 5 to 80 wt. % of the monomeric di- and/or tri-isocyanate used has been converted.

8. The method according to claim 7 , wherein the oligomerization is terminated by deactivation of the catalyst.

9. The method according to one of claims 7 and 8 , characterised wherein unconverted monomer is separated from the reaction mixture.

10. The method according to claim 2 , wherein that the amount of succinonitrile is from 0.001 to 10%.

11. The method according to claim 2 , wherein that the amount of succinonitrile is from 0.01 to 5%.

12. The method according to claim 3 , wherein the aliphatic diisocyanate is selected from the group consisting of hexamethylene diisocyanate (HDI), 2-methylpentane 1,5-diisocyanate, 2,4,4-trimethyl-1,6-hexane diisocyanate, 2,2,4-trimethyl-1,6-hexane diisocyanate and/or 4-isocyanatomethyl-1,8-octane diisocyanate.

13. The method according to claim 3 , wherein the aliphatic diisocyanate is hexamethylene diisocyanate (HDI).

14. The method according to claim 5 , wherein the catalyst is included in an amount of from 5 mol-ppm to 0.1 mol-%, based on the amount of monomeric di- and/or tri-isocyanate.

15. The method according to claim 6 , wherein the method is carried out in the temperature range of from 20 to 180° C.

16. The method according to claim 1 , wherein the method is carried out in the temperature range of from 40 to 150° C.

17. The method according to claim 1 , wherein the method is carried out in the temperature range of from 50 to 90° C.

18. The method according to claim 1 , wherein the oligomerization is terminated when from 10 to 60 wt. % of the monomeric di- and/or tri-isocyanate used has been converted.

19. The method according to claim 8 , wherein the deactivation occurs by one or more members selected from the group consisting of addition of an acid or of a derivative thereof, an acid ester of acids containing phosphorus or sulfur, an acid containing phosphorus or sulfur, adsorptive binding of the catalyst and subsequent separation by filtration, or combinations thereof.

20. The method according to claim 5 , wherein the catalyst comprises a catalyst mixture.

21. The method according to claim 14 , wherein the catalyst comprises a catalyst mixture.

22. A reaction system for producing polyisocyanates containing iminooxadiazinedione groups, the reaction system comprising at least one monomeric di- and/or tri-isocyanate at least one catalyst and succinonitrile, wherein the catalyst is a tetraorganyl-ammonium salt or a tetraorganyl-phosphonium salt, wherein the anions of the tetraorganyl-ammonium salt or tetraorganyl-phosphonium salt are selected from the group: RfCR 1 R 2 COO − , wherein Rf represents a straight-chained or branched perfluoroalkyl radical and R 1 and R 2 independently represent H, straight-chained or branched organyl radicals, fluoride (F − ), di- and/or poly-(hydrogen) fluorides ([F − ×HF) m ]), and wherein m has a numerical value of from 0.001 to 20.

Assignees

• Covestro Deutschland Ag

Inventors

• Richter Frank
• Halpasp Reinhard

Classifications

• C08G18/022

  the polymeric products containing isocyanurate groups · CPC title

• C08G18/166

  Catalysts not provided for in the groups C08G18/18 - C08G18/26 · CPC title

• C08G18/02

  of isocyanates or isothiocyanates only · CPC title

• C07D273/04

  Six-membered rings · CPC title

• C08G18/7887 Primary

  having two nitrogen atoms in the ring · CPC title