Curable coating compositions containing poly activated methylene resins and polyisocyanates

Patent metadata

Field	Value
Publication number	US-11390774-B2
Application number	US-201615759162-A
Country	US
Kind code	B2
Filing date	Sep 9, 2016
Priority date	Sep 11, 2015
Publication date	Jul 19, 2022
Grant date	Jul 19, 2022

Abstract

A curable coating composition includes: (a) a polymer including at least two active methylene functional groups; (b) a polyisocyanate crosslinker; and (c) a transition metal catalyst. Substrates at least partially coated with these coating compositions are further disclosed. Methods for preparing the coating are further disclosed. Multi-layer coatings including these coating compositions are further disclosed.

First claim

The invention claimed is:

1. A curable coating composition that upon curing forms a reaction product of an addition reaction between: (a) a polymer comprising at least two active methylene functional groups, wherein the at least two active methylene functional groups comprise at least one acetoacetate functional group, and an active methylene functional group equivalent weight of the polymer is from 150 to 1,000, and (b) a polyisocyanate crosslinker, wherein the addition reaction occurs between the polyisocyanate crosslinker (b) and an active methylene functional group of the polymer (a) and is catalyzed by (c) a catalyst comprising a zinc complex, wherein an amount of the polymer (a) comprises from 10 to 60 wt %, an amount of the polyisocyanate crosslinker (b) comprises from 1 to 60 wt %, and an amount of the catalyst (c) comprising the zinc complex comprises from greater than 0 to 3 wt % based on a total weight of reactants used to form the reaction product.

2. The curable coating composition of claim 1 , wherein the polymer (a) further comprises at least one hydroxyl, carboxyl, epoxy, alkoxysilane, and/or anhydride functional group.

3. The curable coating composition of claim 1 , further comprising a compound (d) that is different from polymer (a) and comprises at least one active methylene functional group.

4. The curable coating composition of claim 1 , wherein polymer (a) comprises at least one polyacetoacetate-containing polyacrylate or polyacetoacetate-containing polyester, or both.

5. The curable coating composition of claim 4 , wherein the polymer (a) comprises a polyacetoacetate-containing polyacrylate, wherein the polyacrylate comprises less than 85 weight % of monomers the homopolymers thereof have a glass transition temperature (Tg) of less than −40° C.

6. The curable coating composition of claim 1 , wherein the polyisocyanate crosslinker comprises isophorone diisocyanate, 1,6-hexamethylenediisocyanate, isocyanurates, iminooxadiazindiones, biurets, allophanates, uretdiones, dimers, trimers, and/or mixture thereof.

7. The curable coating composition of claim 1 , wherein a ratio of isocyanate functional groups to active methylene functional groups is within a range of from 2.5:1 to 0.5:1.

8. The curable coating composition of claim 1 , wherein the amount of the polymer (a) comprises from 30-60 wt %; the amount of the polyisocyanate crosslinker comprises from 31-60 wt %; and an amount of the catalyst (c) comprising the zinc complex comprises from greater than 0 to 3 wt %, based on the total weight of reactants used to form the reaction product.

9. A substrate at least partially coated with a coating formed from a curable coating composition that upon curing forms a reaction product of an addition reaction between: (a) a polymer comprising at least two active methylene functional groups, wherein the at least two active methylene functional groups comprise at least one acetoacetate functional group, and an active methylene functional group equivalent weight of the polymer is from 150 to 1,000, and (b) a polyisocyanate crosslinker, wherein the addition reaction occurs between the polyisocyanate crosslinker (b) and an active methylene functional group of the polymer (a) and is catalyzed by (c) a catalyst comprising a zinc complex, wherein an amount of the polymer (a) comprises from 10 to 60 wt %, an amount of the polyisocyanate crosslinker (b) comprises from 1 to 60 wt % and an amount of the catalyst (c) comprising the zinc complex comprises from greater than 0 to 3 wt %, based on a total weight of reactants used to form the reaction product;
wherein the coating formed from the curable coating composition forms a monocoat; and
wherein the curable coating composition further comprises a pigment.

10. A multi-layer coating comprising: a topcoat coating layer formed from a curable coating composition that upon curing forms a reaction product of an addition reaction between: (a) a polymer comprising at least two active methylene functional groups, wherein the at least two active methylene functional groups comprise at least one acetoacetate functional group, and an active methylene functional group equivalent weight of the polymer is from 150 to 1,000, and (b) a polyisocyanate crosslinker, wherein the addition reaction occurs between the polyisocyanate crosslinker (b) and an active methylene functional group of the polymer (a) and is catalyzed by (c) a catalyst comprising a zinc complex, wherein an amount of the polymer (a) comprises from 10 to 60 wt %, an amount of the polyisocyanate crosslinker (b) comprises from 1 to 60 wt % and an amount of the catalyst (c) comprising the zinc complex comprises from greater than 0 to 3 wt %, based on a total weight of reactants used to form the reaction product; and a second coating layer under the topcoat coating layer, the second coating layer prepared from a coating composition that is different from the curable coating composition of the topcoat coating layer and which comprises a film-forming resin.

11. The multilayer coating of claim 10 , wherein the curable coating composition further comprises a pigment.

12. The multilayer coating of claim 10 , wherein the film-forming resin of the second coating layer comprises an epoxy or polyurethane resin.

13. The multilayer coating of claim 10 , wherein the second coating layer further comprises a pigment, and wherein the topcoat coating layer is a clear coating layer.

14. A method for preparing a coating comprising:
(i) applying the curable coating composition of claim 1 onto at least a portion of a substrate as a topcoat layer; and
(ii) curing the curable coating composition at at least 20° C. for less than 4 hours to form a coating on the substrate.

15. The method of claim 14 , wherein the substrate is metal.

16. The method of claim 15 , wherein the metal is a pretreated metal.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Breon Jonathan P
• Deng Jun
• Li Linlin
• Schwendeman John E
• Millero Jr Edward R

Classifications

• C09D175/04 Primary

  Polyurethanes · CPC title

• C08G18/34

  Carboxylic acids; Esters thereof with monohydroxyl compounds · CPC title

• C08G18/2895

  Compounds containing active methylene groups · CPC title

• B05D3/007

  After-treatment · CPC title

• C09D183/06

  containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence) · CPC title