Acid-Catalyzed Curable Coating Compositions Containing 1,1-Di-Activated Vinyl Compounds and Related Coatings and Processes

Patent metadata

Field	Value
Publication number	US-2019161637-A1
Application number	US-201716320671-A
Country	US
Kind code	A1
Filing date	Jul 26, 2017
Priority date	Jul 26, 2016
Publication date	May 30, 2019
Grant date	—

Abstract

Acid-catalyzed curable coating compositions containing 1,1-di-activated vinyl compounds are described, including multi-layer coatings. Also provided are processes for coating substrates with coating compositions comprising 1,1-di-activated vinyl compounds, Also provided are coated articles comprising coatings formed from coating compositions comprising 1,1-di-activated vinyl compounds.

First claim

What is claimed is:

1 . An coating comprising:
a polymeric resin; an acid curing catalyst; and a 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof.

2 . The coating of claim 1 , wherein the polymeric resin comprises a carbamate-functional resin, an epoxy-functional resin, an amino-functional resin, a siloxane resin, a melamine resin, a phenolic resin, or a combination of any thereof.

3 . The coating of claim 1 , wherein the polymeric resin comprises polymer molecules comprising any combination of carbamate groups, epoxy groups, siloxane groups, amino groups, melamine groups, or phenol-formaldehyde groups.

4 . The coating of claim 1 , wherein the polymeric resin comprises a carbamate-functional resin.

5 . The coating of claim 4 , wherein the carbamate-functional resin comprises a carbamate-functional acrylic resin.

6 . The coating of claim 4 , wherein the carbamate-functional resin comprises a carbamate-functional and hydroxy-functional acrylic resin.

7 . The coating of claim 4 , further comprising a melamine-formaldehyde resin.

8 . The coating of claim 1 , wherein the acid curing catalyst comprises a strong acid.

9 . The coating of claim 1 , wherein the 1,1-di-activated vinyl compound comprises a methylene dicarbonyl compound, a dihalo vinyl compound, a dihaloalkyl disubstituted vinyl compound, or a cyanoacrylate compound, or a multifunctional form of any thereof, or a combination of any thereof.

10 . The coating of claim 9 , wherein the 1,1-di-activated vinyl compound comprises:
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.

11 . The coating of claim 10 , wherein the 1,1-di-activated vinyl compound comprises:
diethyl methylene malonate; and a multifunctional form of diethyl methylene malonate comprising a transesterification adduct of diethyl methylene malonate and at least one polyol.

12 . The coating of claim 11 , wherein the transesterification adduct of diethyl methylene malonate and at least one polyol comprises a transesterification adduct of diethyl methylene malonate and a diol.

13 . The coating of claim 12 , wherein the diol comprises an alkane diol.

14 . The coating of claim 13 , wherein the alkane diol comprises 1,5-pentane diol and/or 1,6-hexanediol.

15 . 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 is formed from a coating composition comprising:
a carbamate-functional resin
an acid curing catalyst; and
a 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof.

16 . The multi-layer coating of claim 15 , wherein the 1,1-di-activated vinyl compound comprises a methylene dicarbonyl compound, a dihalo vinyl compound, a dihaloalkyl disubstituted vinyl compound, or a cyanoacrylate compound, or a multifunctional form of any thereof, or a combination of any thereof.

17 . The multi-layer coating of claim 16 , wherein the 1,1-di-activated vinyl compound comprises:
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.

18 . The multi-layer coating of claim 17 , wherein the 1,1-di-activated vinyl compound comprises:
diethyl methylene malonate; and a multifunctional form of diethyl methylene malonate comprising a transesterification adduct of diethyl methylene malonate and at least one polyol.

19 . The multi-layer coating of claim 18 , wherein the transesterification adduct of diethyl methylene malonate and at least one polyol comprises a transesterification adduct of diethyl methylene malonate and a diol.

20 . The multi-layer coating of claim 19 , wherein the diol comprises an alkane diol.

21 . The multi-layer coating of claim 20 , wherein the alkane diol comprises 1,5-pentane diol and/or 1,6-hexanediol.

22 . The multi-layer coating of claim 15 , wherein the carbamate-functional resin comprises a carbamate-functional acrylic resin.

23 . The multi-layer coating of claim 15 , wherein the carbamate-functional resin comprises a carbamate-functional and hydroxy-functional acrylic resin.

24 . The multi-layer coating of claim 15 , wherein the coating composition forming the second coating layer further comprises a melamine-formaldehyde resin.

25 . The multi-layer coating of claim 15 , wherein the first coating layer is formed from a coating composition comprising an amine compound.

26 . The multi-layer coating of claim 25 , wherein the amine compound comprises 2-15 percent by solids weight of the coating composition forming the first coating layer.

27 . The multi-layer coating of claim 25 , wherein the amine compound has a standard boiling point temperature less than 165° C.

28 . The multi-layer coating of claim 25 , wherein the amine compound has a pKa greater than 9.5, measured in water at 25° C., and 1 atmosphere pressure.

29 . The multi-layer coating of claim 25 , wherein the amine compound comprises a tertiary amine compound.

30 . The multi-layer coating of claim 29 , wherein the tertiary amine compound comprises 2-(dimethylamino)ethanol.

31 . The multi-layer coating of claim 25 , wherein the coating composition forming the first coating layer further comprises a polyester resin, an acrylic resin, and a melamine-formaldehyde resin.

32 . A multi-layer coating comprising:
a first coating layer applied over at least a portion of a substrate; a second coating layer applied over at least a portion of the first coating layer, wherein the second coating layer is formed from a coating composition comprising 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof; and a third coating layer applied over at least a portion of the second coating layer, wherein the third coating layer is formed from a coating composition comprising a carbamate-functional resin and an acid curing catalyst.

33 . The multi-layer coating of claim 32 , wherein the 1,1-di-activated vinyl compound comprises a methylene dicarbonyl compound, a dihalo vinyl compound, a dihaloalkyl disubstituted vinyl compound, or a cyanoacrylate compound, or a multifunctional form of any thereof, or a combination of any thereof.

34 . The multi-layer coating of claim 33 , wherein the 1,1-di-activated vinyl compound comprises:
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.

35 . The multi-layer coating of claim 34 , wherein the 1,1-di-activated vinyl compound comprises:
diethyl methylene malonate; and a multifunctional form of diethyl methylene malonate comprising a transesterification adduct of diethyl methylene malonate and at least one polyol.

36 . The multi-layer coating of cl

Assignees

• Ppg Ind Ohio Inc

Inventors

• Olson Kurt G
• Gottumukkala Aditya
• Niederst Craig D
• Fenn David R
• Boggs Carol L

Classifications

• C09D7/63

  organic · CPC title

• B05D7/574

  at least some layers being let to dry at least partially before applying the next layer (B05D7/577 takes precedence) · CPC title

• C09D7/65

  macromolecular (C09D7/41-C09D7/48 take precedence) · CPC title

• C08L61/28

  with melamine · CPC title

• C09D133/14 Primary

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title