Multi-layer curable compositions containing 1,1-di-activated vinyl compound products and related processes

Patent metadata

Field	Value
Publication number	US-10987697-B2
Application number	US-201716320534-A
Country	US
Kind code	B2
Filing date	Jul 26, 2017
Priority date	Jul 26, 2016
Publication date	Apr 27, 2021
Grant date	Apr 27, 2021

Abstract

Multi-layer coatings comprising polymerization reaction products of 1,1-di-activated vinyl compounds are described. Also provided are processes for coating substrates with curable compositions comprising 1,1-di-activated vinyl compounds. Also provided are articles coated with this composition.

First claim

What is claimed is:

1. A multi-layer curable composition comprising:
a first curable composition layer applied over at least a portion of a substrate; and
a second curable composition layer applied over at least a portion of the first curable composition layer;
wherein the first curable composition layer and the second curable composition layer both independently comprise a polymeric resin; and
wherein the first curable composition layer and/or the second curable composition layer, when cured, comprise a polymerization reaction of a dialkyl methylene malonate, a diaryl methylene malonate, a multifunctional form of a dialkyl methylene malonate, or a multifunctional form of a diaryl methylene malonate, or a combination of any thereof.

2. The multi-layer curable composition of claim 1 , wherein the first curable composition layer and/or the second curable composition layer, when cured, comprise a polymerization reaction product of a multifunctional form of a dialkyl methylene malonate, or a multifunctional form of a diaryl methylene malonate, or a combination of any thereof.

3. The multi-layer curable composition of claim 1 , wherein the first curable composition layer and/or the second curable composition layer, when cured, comprise a polymerization reaction product of diethyl methylene malonate and a multifunctional form of diethyl methylene malonate, wherein the multifunctional form of diethyl methylene malonate comprises a transesterification adduct of diethyl methylene malonate and at least one polyol.

4. The multi-layer curable composition of claim 1 , wherein:
(i) the first curable composition layer comprises an activator compound that activated polymerization reactions in the second curable composition layer when the second curable composition layer was applied over the first curable composition layer; or
(ii) the second curable composition layer comprises an activator compound that activates polymerization reactions in the first curable composition layer upon application of the second curable composition layer over the first curable composition layer.

5. The multi-layer curable composition of claim 4 , wherein the activator compound comprises a tertiary amine compound.

6. The multi-layer curable composition of claim 5 , wherein the activator compound comprises 2-(dimethylamino)ethanol and/or 1,4-diazabicyclo[2.2.2]octane.

7. The multi-layer curable composition of claim 4 , wherein the activator compound comprises an ionic liquid.

8. The multi-layer curable composition of claim 1 , wherein the first curable composition layer comprises a curable composition that cures when heated at a temperature of less than 500° C.;
and wherein the second curable composition layer comprises the polymerization reaction product.

9. The multi-layer curable composition of claim 1 , wherein the first curable composition layer comprises a thermoset resin comprising acrylic resin, polyester resin, polyurethane resin, polyurea resin, polyether resin, polythioether resin, polycarbonate resin, polycarbamate resin, epoxy resin, phenolic resin, or aminoplast resin, or a combination of any thereof, and wherein the second curable composition layer comprises a clearcoat layer comprising the polymerization reaction product.

10. The multi-layer curable composition of claim 1 , wherein the first curable composition layer comprises the polymerization reaction product, and wherein the first curable composition layer is applied directly onto a metallic substrate.

11. The multi-layer curable composition of claim 1 , wherein the first curable composition layer comprises the polymerization reaction product, and wherein the first curable composition layer is applied directly onto a non-metallic substrate.

12. The multi-layer curable composition of claim 11 , wherein the non-metallic substrate is an automobile component.

13. The multi-layer curable composition of claim 1 , wherein the substrate comprises an electrodeposited curable composition layer and the first curable composition layer is applied over the electrodeposited curable composition layer.

14. The multi-layer curable composition of claim 1 , wherein the curable composition layer comprising the polymerization reaction product further comprises an extender.

15. The multi-layer curable composition of claim 14 , wherein the extender comprises an anhydride-containing vinyl polymer.

16. An article comprising the multi-layer curable composition of claim 1 deposited over a surface of the article.

17. The article of claim 16 , wherein the article comprises a vehicle component or a free-standing structure.

18. A process for applying a curable composition to a substrate comprising:
applying a first curable composition layer over at least a portion of a substrate;
applying a second curable composition layer over at least a portion of the first curable composition layer; and
curing the first curable composition layer and/or the second curable composition layer;
wherein the first curable composition layer and the second coating layer both independently comprise a polymeric resin; and
wherein the first curable composition layer and/or the second curable composition layer, when cured, comprise a polymerization reaction product of a dialkyl methylene malonate, a diaryl methylene malonate, a multifunctional form of a dialkyl methylene malonate, or a multifunctional form of a diaryl methylene malonate, or a combination of any thereof.

19. The process of claim 18 , wherein the curing of the first curable composition layer and/or the second curable composition layer comprises applying an activator solution over and/or under at least a portion of the first curable composition layer and/or the second curable composition layer.

20. The process of claim 19 , wherein the activator solution comprises a tertiary amine compound.

21. The process of claim 18 , wherein:
(i) the first curable composition layer comprises an activator compound, and wherein the curing of the second curable composition layer comprises activating a polymerization reaction in the second curable composition layer with the activator compound in the first curable composition layer; or
(ii) the second curable composition layer comprises an activator compound, and wherein the curing of the first curable composition layer comprises activating a polymerization reaction in the first curable composition layer with the activator compound in the second coating layer.

22. The process of claim 21 , wherein the activator compound comprises a tertiary amine compound.

23. The process of claim 18 , wherein at least one of the first curable composition layer and/or the second curable composition layer, when cured, comprises a polymerization reaction product of a multifunctional form of a dialkyl methylene malonate, or a multifunctional form of a diaryl methylene malonate, or a combination thereof.

24. The process of claim 18 , wherein the first curable composition layer and/or the second curable composition layer comprises a polymerization reaction product of diethyl methylene malonate and a multifunctional form of diethyl methylene malonate, wherein the multifunctional form of diethyl methylene malonate comprises a transesterification adduct of diethyl methylene malonate and at least one polyol.

25. The process of claim 18 , wherein the first curable composition layer comprises a curable composition that cures when heated at a temperature of less th

Assignees

• Ppg Ind Ohio Inc

Inventors

• Moravek Scott J
• Connor Daniel
• Powell Adam B
• Olson Kurt G
• Swarup Shanti
• Harris Caroline S
• Schwartzmiller Davina J
• Gottumukkala Aditya
• Furar John M
• Eibon William E
• Condie Allison G
• Sadvary Richard J
• Sisco Scott W
• Tyebjee Shiryn

Classifications

• C09D4/00 Primary

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• C08L35/02

  Homopolymers or copolymers of esters (C08L35/06, C08L35/08 take precedence) · CPC title

• B05D2518/00

  Other type of polymers · CPC title

• B05D2401/20

  Aqueous dispersion or solution · CPC title

• C08K5/17

  Amines; Quaternary ammonium compounds · CPC title