Polyurethane coating compositions containing 1,1-di-activated vinyl compounds and related coatings and processes

Patent metadata

Field	Value
Publication number	US-11078376-B2
Application number	US-201716320604-A
Country	US
Kind code	B2
Filing date	Jul 26, 2017
Priority date	Jul 26, 2016
Publication date	Aug 3, 2021
Grant date	Aug 3, 2021

Abstract

Polyisocyanate-cured coating compositions containing 1,1-di-activated vinyl compounds are described. Also provided are coatings formed from coating compositions comprising 1,1-di-activated vinyl compounds, including multi-layer coatings. Also provided are processes for coating substrates with coating compositions comprising 1,1-di-activated vinyl compounds. Also provided are articles employing the coatings described herein.

First claim

What is claimed is:

1. A coating composition comprising:
(A) a polyfunctional resin; and
(B) a crosslinker composition comprising:
(b1) a polyisocyanate compound; and
(b2) a 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof, wherein the 1,1-di-activated vinyl compound comprises a methylene dicarbonyl compound, a dihaloalkyl disubstituted vinyl compound, a multifunctional form of a methylene dicarbonyl compound, a multifunctional form of a dihaloalkyl compound, a multifunctional form of a dihaloalkyl disubstituted vinyl compound, or combination thereof;

wherein a mixture of components (A) and (B) form a coating composition.

2. A coating composition of claim 1 , wherein the polyfunctional resin is a polyol.

3. A coating composition of claim 1 , wherein the polyfunctional resin is a polyamine.

4. A coating crosslinker composition comprising:
a polyisocyanate compound; and
a 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof, wherein the 1,1-di-activated vinyl compound comprises a methylene dicarbonyl compound, a dihaloalkyl disubstituted vinyl compound, a multifunctional form of a methylene dicarbonyl compound, a multifunctional form of a dihaloalkyl compound, a multifunctional form of a dihaloalkyl disubstituted vinyl compound, or combination thereof.

5. A multi-layer coating comprising:
a first coating layer applied over at least a portion of a substrate; and
a second coating layer applied over at least a portion of the first coating layer;
wherein the second coating layer comprises:
a reaction product of a first polyfunctional resin and a polyisocyanate; and
one or more of:
an addition reaction product of:
a second polyfunctional resin; and
a 1,1-di-activated vinyl compound, or a multifunctional form

thereof, or a combination thereof; and/or
a polymerization reaction product of the 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof,
wherein the 1,1-di-activated vinyl compound comprises a methylene dicarbonyl compound, a dihaloalkyl disubstituted vinyl compound, a multifunctional form of a methylene dicarbonyl compound, a multifunctional form of a dihaloalkyl compound, a multifunctional form of a dihaloalkyl disubstituted vinyl compound, or combination thereof.

6. A multi-layer coating of claim 5 wherein the first polyfunctional resin, the second polyfunctional resin, or a combination thereof is a polyol.

7. A multi-layer coating of claim 5 wherein the first polyfunctional resin, the second polyfunctional resin, or a combination thereof is a polythiol.

8. A multi-layer coating of claim 5 wherein the first polyfunctional resin, the second polyfunctional resin, or a combination thereof is a polyamine.

9. The multi-layer coating of claim 5 , wherein the second coating layer comprises an addition reaction product of:
(1) a polyfunctional resin comprising a polyol; and
(2) 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.

10. The multi-layer coating of claim 9 , wherein the transesterification adduct of diethyl methylene malonate and at least one polyol comprises a transesterification adduct of diethyl methylene malonate and a diol.

11. The multi-layer coating of claim 5 , wherein the first coating layer comprises an activator compound that activated addition reactions and/or polymerization reactions in the second coating layer when the second coating layer was applied over the first coating layer.

12. The multi-layer coating of claim 11 , wherein the activator compound comprises a tertiary amine compound.

13. The multi-layer coating of claim 5 , wherein the second coating layer comprises a clearcoat layer.

14. An article comprising the multi-layer coating of claim 5 deposited on a surface of the article.

15. The article of claim 14 , wherein the article comprises a vehicle component or a component of a free-standing structure.

16. A process for coating a substrate comprising:
applying a first coating layer over at least a portion of a substrate;
applying a second coating layer over at least a portion of the first coating layer; and
curing the second coating layer;
wherein the second coating layer comprises a coating composition comprising:
a polyol resin;
polyisocyanate; and
a 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof, wherein the 1,1-di-activated vinyl compound comprises a methylene dicarbonyl compound, a dihaloalkyl disubstituted vinyl compound, a multifunctional form of a methylene dicarbonyl compound, a multifunctional form of a dihaloalkyl compound, a multifunctional form of a dihaloalkyl disubstituted vinyl compound, or combination thereof.

17. The process of claim 16 , wherein the curing of the second coating layer comprises a multiple-curing mechanism comprising:
crosslinking reactions between the polyol resin and the polyisocyanate; and
one or more of:
polymerization reactions of the 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof; and/or
addition reactions between the polyol resin and the 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof.

18. The process of claim 16 , wherein:
the first coating layer comprises an activator compound;
the curing of the second coating layer comprises activating a polymerization reaction and/or an addition reaction in the second coating layer with the activator compound in the first coating layer; and
the 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof (1) is polymerized and/or (2) reacts with the polyol resin to produce an addition reaction product.

19. The process of claim 18 , wherein the activator compound comprises a tertiary amine compound.

20. The process of claim 17 , wherein the second coating layer, when cured, comprises:
a reaction product of the polyol resin and the polyisocyanate; and
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.

21. The process of claim 17 , wherein the second coating layer, when cured, comprises:
a reaction product of the polyol resin and the polyisocyanate; and
an addition reaction product of:
(1) the polyol resin; and
(2) 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.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Gottumukkala Aditya
• Sisco Scott W
• Fenn David R
• Moyano Daniel F
• Olson Kurt G
• Luchansky Matthew S
• Sadvary Richard J
• Tyebjee Shiryn
• Harris Caroline S
• Swarup Shanti

Classifications

• B05D2508/00

  Polyesters · CPC title

• C08G71/04

  Polyurethanes · CPC title

• B05D7/534

  the first layer being let to dry at least partially before applying the second layer (B05D7/538 takes precedence) · CPC title

• C08G18/797

  containing carbodiimide and/or uretone-imine groups · CPC title

• C08G18/4018

  Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48 · CPC title