Zinc ketoiminate complexes as catalysts for the production of polyurethanes

Patent metadata

Field	Value
Publication number	US-10787464-B2
Application number	US-201816648345-A
Country	US
Kind code	B2
Filing date	Sep 14, 2018
Priority date	Oct 17, 2017
Publication date	Sep 29, 2020
Grant date	Sep 29, 2020

Abstract

The use of zinc ketoiminate complexes in the production of polyurethanes is described, wherein the zinc ketoiminate complexes are obtainable by reacting a zinc compound with certain ketimines.

First claim

The invention claimed is:

1. A process of making a zinc ketoiminate complex comprising the steps of
reacting a zinc compound (A) with ketimines (B) of the formula (I) and alcohol or polyether

where R 1 and R 3 are organic radicals having from 1 to 6 carbon atoms, comprising heteroatoms selected from the group consisting of oxygen, nitrogen and halogen atoms,
R 2 is H−,
R 4 is an organic radical having 1 to 4 carbon atoms comprising heteroatoms selected from the group consisting of oxygen, nitrogen and halogen atoms,
R 5 and R 6 are organic radicals having 1 to 6 carbon atoms, comprising heteroatoms selected from the group consisting of oxygen, nitrogen and halogen atoms,
wherein the radicals R 5 and R 6 may also be bonded to form a ring.

2. A process of making a zinc ketoiminate complex-comprising the steps of reacting a zinc compound (A) with ketimines (B) of the formula (I) and alcohol or polyether with ketimines (B) is one of the following compounds

wherein the zinc ketoiminate complex are obtained by reacting a zinc compound (A) with alkoxide or polyether ion previously deprotonated by exposure to suitable basic substances, such that a zinc dialkoxide is formed, which is reacted with previously deprotonated ketimines (B).

3. The process according to claim 1 , wherein the zinc compound (A) is an organozinc compound.

4. The process according to claim 3 , wherein an organozinc compound is used, and the alcohol is added after (A) has been reacted with (B).

5. The process according to claim 3 , wherein the zinc ketoiminate complex are obtained by reaction of zinc salt with previously deprotonated ketimines (B) and alkoxide, which have been converted into the anionic form by exposure to a suitable base.

6. The process according to claim 3 , wherein the zinc ketoiminate complex are obtained by reacting a zinc salt with alkoxide or polyether ion previously deprotonated by exposure to suitable basic substances, such that a zinc dialkoxide is formed, which is reacted with previously deprotonated ketimines (B).

7. The process according to claim 1 , wherein the zinc ketoiminate complex is used as catalyst in the production of a polyurethane.

8. The process according to claim 1 , wherein a PU coating, PU adhesive, PU sealant or PU elastomer is produced.

9. The process according to claim 7 , wherein in the production of the polyurethane, a composition is prepared which comprises at least one zinc ketoiminate complex, at least one polyol component and at least one isocyanate component, and this composition is reacted.

10. The process according to claim 1 , wherein the zinc ketoiminate complex is formula Zn k (L) m (Y) n ,
where k is an integer from 1 to 20,
m is 1, 2, 3 or 4,
n is 0, 1, 2, 3 or 4,
Y is a negatively charged ligand selected from the group consisting of an alkoxide ion, phenolate ion, a polyoxyalkylene radical or the radical of a polyoxyalkylated compound, and L is a ligand of formula (II),

where R 1 to R 6 are R 1 to R 6.

11. A composition comprising at least one polyol component, wherein the composition comprises at least one zinc ketoiminate complex as defined in claim 1 .

12. The composition according to claim 11 , wherein the composition comprises at least one isocyanate component.

13. A polyurethane made with the zinc ketoiminate complex according to claim 1 .

14. The polyurethane according to claim 13 , wherein the polyurethane system is a PU coating, PU adhesive, PU sealant or PU elastomer.

15. The polyurethane according to claim 14 , wherein the polyurethane comprises a proportion by mass of zinc ketoiminate complex in the polyurethane system of 0.005 to 10% by weight.

16. A process of making a zinc ketoiminate complex-comprising the steps of reacting a zinc compound (A) with ketimines (B) of the formula (I) and alcohol or polyether with ketimines (B) is one of the following compounds

17. The process according to claim 3 , wherein an organozinc compound is diethylzinc, and the alcohol is selected from the group consisting of phenol, cardanol, diethylene glycol monoethyl ether or poly(oxypropylene) monobutyl ether.

18. The process according to claim 3 , wherein the zinc compound (A) is zinc chloride.

19. The process according to claim 3 , wherein the zinc ketoiminate complex are obtained by reacting a zinc iodide, with alkoxide or polyether ion previously deprotonated by exposure to suitable basic substances, such that a zinc dialkoxide is formed, which is reacted with previously deprotonated ketimines (B).

20. A polyurethane obtained by the process according to claim 2 .

Assignees

• Evonik Operations Gmbh

Inventors

• Fiedel Michael
• GüNTHER THOMAS
• Glos Martin
• Ferenz Michael
• Eilbracht Christian
• Knott Wilfried
• Schulz Stephan
• Dittrich Dennis

Classifications

• C07F3/06 Primary

  Zinc compounds · CPC title

• C08G18/222 Primary

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