Iminooxadiazinedione polyisocyanates

Patent metadata

Field	Value
Publication number	US-9926402-B2
Application number	US-201414562813-A
Country	US
Kind code	B2
Filing date	Dec 8, 2014
Priority date	Dec 10, 2013
Publication date	Mar 27, 2018
Grant date	Mar 27, 2018

Abstract

The present invention relates to a process for producing polyisocyanates comprising reacting an isocyanate component in the presence of a mono- or multinuclear complex of titanium, zirconium and/or hafnium as catalyst to give polyisocyanates having a content of iminooxadiazinedione groups of ≥20 mol % based on the total amount of isocyanurate and iminooxadiazinedione groups. The present invention also provides polyisocyanates obtainable by the process according to the invention and both polyurethanes and polyureas obtainable by reacting the polyisocyanates with at least one hydroxy-functional or amino-functional component respectively.

First claim

The invention claimed is:

1. A process for producing a polyisocyanate containing isocyanurate and iminooxadiazinedone groups comprising reacting an isocyanate component in the presence of a catalyst to give polyisocyanates having a content of iminooxadiazinedione groups of ≥20 mol % based on the total amount of isocyanurate and iminooxadiazinedione groups, wherein the reaction is carried out at a temperature in the range between 105° C. and 150° C., wherein the catalyst is at least one carboxylate of general formulae (II) or (III)

where
M is titanium, zirconium or hafnium,
R 5 , R 6 , R 7 and R 8 are identical or different radicals and are each a saturated or unsaturated, linear or branched aliphatic or cycloaliphatic, optionally substituted aromatic or araliphatic radical which can comprise 1 to 18 carbon atoms and optionally up to 3 heteroatoms selected from oxygen, sulphur, nitrogen, and optionally up to 3 oxygen atoms and where R 5 , R 6 , R 7 and R 8 in formula (II) and R 5 and R 6 in formula (III) can also form, in any combination with one another together with M and at least two oxygen atoms and optionally further nitrogen or oxygen atoms, heterocyclic rings having 3 to 6 carbon atoms, and can preferably form, together with M and two oxygen atoms, heterocyclic rings having 2 or 3 carbon atoms.

2. The process according to claim 1 , wherein the catalyst is employed in an amount of from 0.0005% to 2.0% by weight, based on the isocyanate component.

3. The process according to claim 1 , wherein the isocyanate component is at least one aliphatic, cycloaliphatic or araliphatic isocyanate, preferably at least one aliphatic and/or araliphatic diisocyanate and more preferably at least 1,6-diisocyanatohexane, 1,3- or 1,4-bis(isocyanatomethyl)benzene.

4. The process according to claim 1 , wherein the isocyanate component is at least 1,6-diisocyanatohexane, 1,3- or 1,4-bis(isocyanatomethyl)benzene.

5. The process according to claim 1 , wherein the isocyanate component is mixed with a hydroxy-functional component and reacted in the presence of the catalyst to give the polyisocyanate.

6. The process according to claim 5 , wherein the hydroxy-functional component comprises up to 0.0049% by weight, based on the isocyanate component, of phenolic hydroxy-functional compounds.

7. The process according to claim 5 , wherein the hydroxy-functional component is free of phenolic hydroxy-functional compounds.

8. The process according to claim 5 , wherein the aliphatic hydroxy-functional compound comprises at least one linear or branched, optionally substituted mono-, di- or trialcohol having 1 to 18 carbon atoms.

9. The process according to claim 1 , wherein the catalyst remains in the polyisocyanate.

10. A polyisocyanate obtained by a process according to claim 1 , wherein the catalyst remains in the polyisocyanate.

11. The polyisocyanate according to claim 1 , wherein some or all of the isocyanate groups of the polyisocyanate have been reacted with at least one blocking agent.

12. A polyurethane obtained by reacting the polyisocyanate according to claim 10 with at least one hydroxy-functional component.

13. A polyurea obtained by reacting the polyisocyanate according claim 10 with at least one amino-functional component.

14. The process according to claim 1 , wherein the at least one carboxylate of formula (II) is selected from the group consisting of titanium tetra-2-ethylhexanoate, titanium tetrastearate, titanium tetraacrylate, titanium tetrabenzoate, zirconium tetraacetate, zirconium tetrapropionate, zirconium tetrabutanoate, zirconium tetraoctanoate, zirconium tetra-2-ethylhexanoate, zirconium tetraneodecanoate, zirconium tetrastearate, zirconium oxalate, zirconium glycolate, zirconium lactate, zirconium tetraacrylate, zirconium tetramethacrylate, zirconium tetranaphthenate, hafnium tetraacetate, hafnium oxalate, hafnium tetraoctoate, hafnium tetra-2-ethylhexanoate, and hafnium tetraneodecanoate.

15. The process according to claim 1 , wherein the at least one carboxylate of formula (III) is selected from the group consisting of titanyl acetate, titanyl propionate, titanyl butanoate, titanyl pentanoate, titanyl hexanoate, titanyl 2-ethylhexanoate, titanyl octanoate, zirconyl acetate, zirconyl octanoate, zirconyl decanoate, zirconyl dodecanoate, zirconyl tetradecanoate, zirconyl pentadecanoate, zirconyl stearate, zirconyl dimethacrylate, zirconyl cyclopentanecarboxylate, zirconyl cyclohexanecarboxylate, zirconyl linolate, zirconyl linolenate, zirconyl oleate, zirconyl benzoate and/or zirconyl diphenylacetate.

Assignees

• Bayer Materialscience Ag
• Covestro Deutschland Ag

Inventors

• Laas Hans-Josef
• Mager Dieter

Classifications

• C08G18/092

  oligomerisation to isocyanurate groups · CPC title

• C08G18/222

  metal compounds not provided for in groups C08G18/225 - C08G18/26 · CPC title

• C08G18/00

  Polymeric products of isocyanates or isothiocyanates · CPC title

• C08G18/10 Primary

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• C08G18/022 Primary

  the polymeric products containing isocyanurate groups · CPC title