Process for modifying isocyanates with use of cyclic ammonium salts as catalyst

Patent metadata

Field	Value
Publication number	US-10167358-B2
Application number	US-201615753004-A
Country	US
Kind code	B2
Filing date	Aug 15, 2016
Priority date	Aug 17, 2015
Publication date	Jan 1, 2019
Grant date	Jan 1, 2019

Abstract

The invention relates to a process for modifying isocyanates where at least one organic isocyanate with NCO functionality >1 is oligomerized in the presence of at least one catalyst, characterized in that the catalyst comprises, as isocyanatemodification catalysts, at least one cyclic ammonium salt having a cation of the formula (I) (formula I), where the N-containing substituents R 1 and R 2 are mutually independently identical or different aliphatic, cycloaliphatic, aromatic or araliphatic C, to C 20 moieties which are saturated or unsaturated, linear or branched, optionally substituted and/or interrupted by heteroatoms from the group of oxygen, sulphur and nitrogen, and Y is a substituted or unsubstituted, linear or branched C 2 to C 20 segment optionally interrupted by heteroatoms from the group of oxygen, sulphur and nitrogen or else intempted by aromatic rings, and optionally containing other rings. The invention further relates to the use of such a catalyst.

First claim

The invention claimed is:

1. A process for modifying isocyanates, in which at least one organic isocyanate having an NCO functionality of >1 is oligomerized in the presence of at least one catalyst, characterized in that the catalyst comprises at least one cyclic ammonium salt having a cation of the formula I as catalysts for the isocyanate modification,

wherein the N-substituents R 1 and R 2 are mutually independently identical or different aliphatic, cycloaliphatic, aromatic or araliphatic C 1 -C 20 radicals, which are saturated or unsaturated, linear or branched, optionally substituted and/or interrupted by heteroatoms from the group of oxygen, sulfur and nitrogen and Y is a substituted or unsubstituted, linear or branched C 2 -C 20 segment optionally interrupted by heteroatoms from the group of oxygen, sulfur, nitrogen and also by aromatic rings, and optionally comprising further rings.

2. The process as claimed in claim 1 , characterized in that R 1 and R 2 are mutually independently identical or different C 1 -C 8 -alkyl substituents.

3. The process as claimed in claim 1 , characterized in that R 1 and R 2 in formula I are mutually independently identical or different benzyl radicals optionally substituted on the aromatic ring.

4. The process as claimed in claim 1 , characterized in that segment Y is C 4 -C 6 -alkylene chains optionally substituted and/or interrupted by heteroatoms from the group of oxygen, sulfur, nitrogen and also by aromatic rings and especially has a linear structure.

5. The process as claimed in claim 1 , characterized in that the anion of the cyclic ammonium salt is selected from hydroxide, alkanoate, carboxylate, heterocycles having at least one negatively charged nitrogen atom in the ring, especially azolate, imidazolate, triazolate, tetrazolate, fluoride, hydrogendifluoride, higher polyfluorides or mixtures of these.

6. The process as claimed in claim 1 , characterized in that the oligomerization is conducted in the presence of a solvent and/or additive.

7. The process as claimed in claim 1 , characterized in that the organic isocyanate is selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, 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, isophorone diisocyanate, 1,3- and 1,4-bis(isocyanatomethyl)benzene, 1,3- and 1,4-bis(isocyanatomethyl)cyclohexane or mixtures of these.

8. The process as claimed in claim 1 , characterized in that the catalyst of the formula I is used in an amount between >0.001 and <5 mol %, based on the sum total of the molar amounts of the isocyanate used and of the catalyst.

9. The process as claimed in claim 1 , characterized in that the process is conducted within the temperature range from 0° C. to +250° C.

10. The process as claimed in claim 1 , characterized in that the oligomerization is stopped after 5% to 80% by weight of the organic isocyanate used has been converted.

11. The process as claimed in claim 10 , characterized in that the oligomerization is stopped by deactivating the catalyst, especially by addition of an acid or an acid derivative such as benzoyl chloride, an acidic ester of phosphorus- or sulfur-containing acids, these acids themselves, adsorptive binding of the catalyst and subsequent removal by filtration or combinations thereof.

12. The process as claimed in claim 10 , characterized in that unconverted organic isocyanate is removed from the reaction mixture.

13. The process as claimed in claim 1 , characterized in that R 1 and R 2 are mutually independently identical or different C 1 -C 6 -alkyl substituents.

14. The process as claimed in claim 1 , characterized in that R 1 and R 2 are mutually independently identical or different C 1 -C 8 -alkyl substituents and have a linear structure.

15. The process as claimed in claim 1 , characterized in that the catalyst of the formula I is used in an amount between >0.002 and <2 mol %, based on the sum total of the molar amounts of the isocyanate used and of the catalyst.

16. The process as claimed in claim 1 , characterized in that the process is conducted within the temperature range from 20 to 200° C.

17. The process as claimed in claim 1 , characterized in that the process is conducted within the temperature range from 40 to 150° C.

18. The process as claimed in claim 1 , characterized in that the oligomerization is stopped after 10% to 60% by weight of the organic isocyanate used has been converted.

Assignees

• Covestro Deutschland Ag

Inventors

• Richter Frank

Classifications

• B01J31/0204

  Ethers · CPC title

• B01J27/12

  Fluorides · CPC title

• C08G18/022 Primary

  the polymeric products containing isocyanurate groups · CPC title

• C08G18/2018

  having one nitrogen atom in the ring · CPC title

• C08G18/18

  containing secondary or tertiary amines or salts thereof · CPC title