Treatment of conversion-coated metal substrates with preformed reaction products of catechol compounds and functionalized co-reactant compounds

Patent metadata

Field	Value
Publication number	US-11891534-B2
Application number	US-201916437113-A
Country	US
Kind code	B2
Filing date	Jun 11, 2019
Priority date	Dec 22, 2016
Publication date	Feb 6, 2024
Grant date	Feb 6, 2024

Abstract

The corrosion resistance of conversion-coated metal substrate surfaces is further enhanced by treating such surfaces with aqueous mixtures of preformed reaction products obtained by reacting catechol compounds, such as dopamine or a dopamine salt, and functionalized co-reactant compounds, such as a polyethyleneimine.

First claim

What is claimed is:

1. A method, comprising contacting a surface of a metal substrate having a conversion coating layer thereon with an aqueous mixture comprised of at least one preformed reaction product of at least one catechol compound and at least one co-reactant compound comprised of one or more functional groups reactive with the at least one catechol compound to thereby deposit a seal layer comprising the at least one preformed reaction product on the conversion coating layer; wherein the at least one co-reactant compound comprises at least one linear or branched, oligomeric or polymeric polyethyleneimine having a number average molecular weight of 500 up to 2,000,000, wherein the at least one catechol compound includes at least one amino-functionalized catechol compound or salt thereof, and wherein the pre-formed reaction product comprises 5 to 25% by weight of the at least one catechol compound, based on total weight of the at least one catechol compound and the at least one co-reactant compound.

2. The method of claim 1 , wherein the at least one amino-functionalized catechol compound or salt thereof comprises an aminoalkyl-functionalized catechol compound or salt thereof.

3. The method of claim 1 , wherein the at least one catechol compound includes at least dopamine or a salt thereof.

4. The method of claim 1 , wherein the at least one co-reactant compound further comprises a co-reactant compound comprising one more functional groups reactive with the at least one catechol compound, said functional groups are selected from the group consisting of acrylate groups, methacrylate groups, acrylamide groups, methacrylamide groups, secondary amino groups, primary amino groups, thiol groups and mixtures thereof.

5. The method of claim 1 , wherein the polyethyleneimine comprises a plurality of primary and/or secondary amine groups.

6. The method of claim 1 , wherein the polyethyleneimine comprises a hyper-branched and/or dendritic structure.

7. The method of claim 1 , wherein the at least one preformed reaction product includes at least one preformed reaction product which is polymeric.

8. The method of claim 1 , wherein the at least one preformed reaction product is water soluble and obtained by reacting the at least one catechol compound and the at least one co-reactant compound under oxidative conditions.

9. The method of claim 1 , wherein the at least one preformed reaction product is obtained by reacting the at least one catechol compound with the at least one co-reactant compound in an aqueous reactant mixture at a temperature of from 10 to 100° C. for a time of from 1 to 20 hours in the presence of molecular oxygen.

10. The method of claim 1 , wherein the at least one preformed reaction product is present in the aqueous mixture at a concentration of from 5 to 500 ppm.

11. The method of claim 1 , wherein contacting the conversion-coated metal substrate with the aqueous mixture is carried out for a time of from 10 seconds to 10 minutes at a temperature of 10 to 54° C.

12. The method of claim 1 , wherein the aqueous mixture, when contacted with the surface of the conversion-coated metal substrate, has a pH of from 8.5 to 11.

13. The method of claim 1 , additionally comprising applying at least one paint layer to the sealed conversion-coated metal substrate.

14. The method of claim 13 , wherein applying at least one paint layer comprises electrophoretic coating.

15. The method of claim 1 , wherein the metal substrate having a conversion coating layer thereon has been conversion-coated by zinc phosphating or by deposition of a Group IV metal oxide.

16. An article comprising a metal substrate, a conversion coating layer on at least one surface of the metal substrate, and a seal layer prepared by the method of claim 1 , wherein the catechol is dopamine and the polyethyleneimine comprises a plurality of primary amino and secondary amino groups and has a number average molecular weight of 800 up to 2,000,000, deposited on the conversion coating layer.

17. The article of claim 16 , additionally comprising at least one paint layer on the seal layer.

18. The method of claim 1 , wherein the at least one co-reactant compound further comprises methacrylamidoethyl ethylene urea.

19. The method of claim 1 , wherein the pre-formed reaction product comprises 5 to 20% by weight of the at least one catechol compound, based on the total weight of the at least one catechol compound and the at least one co-reactant compound.

20. The method of claim 19 , wherein the pre-formed reaction product comprises 5 to 15% by weight of the at least one catechol compound, based on the total weight of the at least one catechol compound and the at least one co-reactant compound.

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Vonk Donald Robb
• Rector Louis Patrick

Classifications

• C09D179/02 Primary

  Polyamines · CPC title

• B32B15/04

  comprising metal as the main or only constituent of a layer, {which is} next to another layer of {the same or of} a {different material (next to a bituminous or tarry layer B32B11/08; next to a water-setting substance layer B32B13/06; next to a glass layer B32B17/061; next to a cellulosic plastic layer B32B23/042)} · CPC title

• B32B15/08

  of synthetic resin · CPC title

• C23C22/05 Primary

  using aqueous solutions · CPC title

• C23C22/06

  using aqueous acidic solutions with pH less than 6 · CPC title