Method for isocyanate modification using catalysts with an NPN sequence

Patent metadata

Field	Value
Publication number	US-10131736-B2
Application number	US-201515119179-A
Country	US
Kind code	B2
Filing date	Feb 13, 2015
Priority date	Feb 18, 2014
Publication date	Nov 20, 2018
Grant date	Nov 20, 2018

Abstract

The invention relates to a method for modifying isocyanates, wherein at least one organic monomer isocyanate having an NCO functionality >1 is oligomerised in the presence of at least one catalyst, said method being characterised in that the catalyst comprises at least one specific compound having an NPN sequence selected from compounds of formula I (formula I), and/or from compounds of formula II (formula II) where HX represents an acid with a pKa value ≥2, X− represents the anion of an acid with a pKa value ≥2, and n represents an integer or fractional number between 0 and 20, wherein Y represents R12(R13)N— and/or one or more substituents of the structure of formula III (formula III) and wherein R1 to R19 independently represent identical or different substituents selected from C1-C20 alkyl-, C1-C20 cycloalkyl- and C6-C20 aryl groups, or wherein R1 and R2, R3 and R4, R5 and R6, R7 and R8, R9 and R10, R12 and R13, R14 and R15, R16 and R17, R18 and R19 independently represent identical or different substituents selected from C1-C20 alkylene-, C1-C20 cycloalkylene-, C6-C20 arylene groups, and can form a 3- to 12-membered ring with the N atom joined to the P atom. The invention also relates to the use of a catalyst of this type.

First claim

The invention claimed is:

1. A process for modifying isocyanates, comprising oligomerizing at least one monomeric organic isocyanate having an NCO functionality of >1 in the presence of at least one catalyst,
wherein,
the catalyst comprises
compounds of the formula II

in which X − is the anion of an acid having a pKa≥2, and
wherein the cation of formula II corresponds to the following formula IV:

and X − is selected from the group consisting of F − , HF 2 − , H 2 F 3 − and mixtures thereof.

2. The process according to claim 1 , wherein the acid corresponding to the anion X − has a pKa≥2.5.

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

4. The process according to claim 1 , wherein the monomeric organic isocyanate comprises one or more aliphatic diisocyanates.

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

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

7. The process according to claim 6 , wherein the oligomerization is stopped by deactivating the catalyst.

8. The process according to claim 6 , wherein unconverted monomeric organic isocyanate is separated from the reaction mixture.

9. The process according to claim 2 , wherein the acid corresponding to the anion X − has a pKa≥3.0.

10. The process according to claim 2 , wherein the acid corresponding to the anion X − has a pKa≥3.10.

11. The process according to claim 4 , wherein the one or more aliphatic isocyanates is/are 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(isocyanatomethyl)cyclohexane (H6XDI) and mixtures thereof.

12. The process according to claim 5 , wherein the process is conducted within the temperature range from about 20 to about 180° C.

13. The process according to claim 5 , wherein the process is conducted within the temperature range from 40 to 150° C.

14. The process according to claim 6 , wherein the oligomerization is stopped after about 10% to about 60% by weight of the monomeric organic isocyanate used has been converted.

15. The process according to claim 7 , wherein the deactivation comprises adding an acid or an acid derivative, an acidic ester of phosphorus- or sulfur-containing acids to adsorptively bind the catalyst and removing the catalyst by filtration.

Assignees

• Covestro Deutschland Ag

Inventors

• Richter Frank

Classifications

• C08G18/73

  acyclic · CPC title

• C08G18/02

  of isocyanates or isothiocyanates only · CPC title

• C08G18/095

  oligomerisation to carbodiimide or uretone-imine groups · CPC title

• C07F9/067

  Polyphosphazenes containing the structure [P=N-n] (cyclic compounds C07F9/65812) · CPC title

• C08G18/097

  oligomerisation to urethdione groups · CPC title