Electrodepositable Coating Compositions Containing 1,1-Di-Activated Vinyl Compounds

Patent metadata

Field	Value
Publication number	US-2019153244-A1
Application number	US-201716320658-A
Country	US
Kind code	A1
Filing date	Jul 26, 2017
Priority date	Jul 26, 2016
Publication date	May 23, 2019
Grant date	—

Abstract

Electrodepositable coating compositions containing 1,1-di-activated vinyl compounds are described. The coating compositions produce cured coating layers that exhibit resistance to cratering. The coating compositions can be used in electrodepositable coating composition formulations.

First claim

What is claimed is:

1 . An elecrodepositable coating composition comprising:
(A) a polymer comprising (1) a reactive functional group and/or (2) a salt group or a salt-forming group; and (B) at least one component comprising:
(b1) a 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof;
(b2) a polymerization reaction product of a 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof; and/or
(b3) an addition reaction product of (1) the polymer component (A) and (2) a 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof.

2 . The coating composition of claim 1 , wherein the coating composition is water dispersible.

3 . The coating composition of claim 1 , wherein the polymer component (A) comprises (1) an active hydrogen functional group and (2) a cationic salt group or an anionic salt group.

4 . The coating composition of claim 1 , comprising 0.1-30 percent by weight of component (b1) and/or (b2), based on total weight of resin solids in the coating composition.

5 . The coating composition of claim 1 , comprising 1-15 percent by weight of component (b1) and/or (b2), based on total weight of resin solids in the coating composition.

6 . The coating composition 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.

7 . The coating composition of claim 6 , wherein the 1,1-di-activated vinyl compound comprises:
a dialkyl methylene malonate; a multifunctional form of a dialkyl methylene malonate; a diaryl methylene malonate; or a multifunctional form of a diaryl methylene malonate; or a combination of any thereof.

8 . The coating composition of claim 7 , wherein the 1,1-di-activated vinyl compound comprises:
dimethyl methylene malonate; and/or a multifunctional form of dimethyl methylene malonate comprising a transesterification adduct of dimethyl methylene malonate and at least one polyol.

9 . The coating composition of claim 7 , wherein the 1,1-di-activated vinyl compound comprises:
diethyl methylene malonate; and/or a multifunctional form of diethyl methylene malonate comprising a transesterification adduct of diethyl methylene malonate and at least one polyol.

10 . The coating composition of claim 9 , wherein the 1,1-di-activated vinyl compound comprises a transesterification adduct of diethyl methylene malonate and at least one diol.

11 . The coating composition of claim 10 , wherein the diol comprises an alkane diol.

12 . The coating composition of claim 11 , wherein the alkane diol comprises 1,5-pentane diol and/or 1,6-hexanediol.

13 . The coating composition of claim 1 , wherein the component (B) comprises the polymerization reaction product (b2) of reactants comprising:
a dialkyl methylene malonate; and/or a multifunctional form of the dialkyl methylene malonate comprising a transesterification adduct of the dialkyl methylene malonate and at least one polyol.

14 . The coating composition of claim 1 , wherein the component (B) comprises the addition reaction product (b3) of reactants comprising:
(i) the polymer component (A) comprising (1) an active hydrogen functional group and (2) a cationic salt group or an anionic salt group; and (ii) a dialkyl methylene malonate and/or a multifunctional form of the dialkyl methylene malonate comprising a transesterification adduct of the dialkyl methylene malonate and at least one polyol.

15 . The coating composition of claim 1 , wherein the polymer component (A) comprises an amine-functional polyepoxide polymer, an amine-functional polyacrylate polymer, an amine-functional polyurethane and/or polyurea polymer, an amine-functional polyester polymer, an amine-functional polyether polymer, an acid-functional polyepoxide polymer, an acid-functional polyacrylate polymer, an acid-functional polyurethane and/or polyurea polymer, an acid-functional polyester polymer, an acid-functional polyether polymer, a sulfonium-functional polyepoxide polymer, a sulfonium-functional polyacrylate polymer, a sulfonium-functional polyurethane and/or polyurea polymer, a sulfonium-functional polyester polymer, or a sulfonium-functional polyether polymer, or a combination of any thereof.

16 . The coating composition of claim 1 , wherein the polymer component (A) comprises a polyepoxide-amine adduct.

17 . An article comprising a coating layer deposited over a surface of the article, wherein the coating layer comprises the coating composition of claim 1 .

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

19 . A process for the production of a coating composition comprising:
reacting (A) a polymer comprising an active hydrogen group and (B) a 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof, to form a resin product; treating the resin product with an acid to form cationic salt groups or base to form anionic salt groups on the polymer; and dispersing the resin product in water.

20 . The process of claim 19 , wherein:
the reacting step comprises reacting (A) a polymer comprising an active hydrogen group and (B) a 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof, to form a resin product; and the treating step comprises treating the resin product with an acid to form cationic salt groups on the polymer.

21 . The process of claim 19 , wherein the resin product comprises a polymerization reaction product of component (B).

22 . The process of claim 19 , wherein the component (B) is reacted during the synthesis of component (A).

23 . The process of claim 19 , wherein the component (B) is reacted during the dispersion of the resin product.

24 . The process of claim 19 , wherein the resin product comprises an addition reaction product of components (A) and (B).

25 . The process of claim 19 , wherein the component (B) is reacted during the formulation of a an electrodepositable coating composition comprising:
(A) a polymer comprising (1) a reactive functional group and/or (2) a salt group or a salt-forming group; and (B) at least one component comprising:
(b1) a 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof;
(b2) a polymerization reaction product of a 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof; and/or
(b3) an addition reaction product of (1) the polymer component (A) and (2) a 1,1-di-activated vinyl compound, or a multifunctional form thereof, or a combination thereof.

26 . The process of claim 19 , wherein component (B) comprises a 1,1-di-activated vinyl compound comprising dimethyl methylene malonate and/or diethyl methylene malonate.

27 . The process of claim 19 , wherein component (B) comprises:
diethyl methylene malonate; and/or a multifunctional form of diethyl methylene malonate comprising a transesterification adduct of diethyl methylene malonate and at least one polyol.

28 . The process of claim 19 , wherein the active hydrogen group-containing polymer comprises a polyepoxide

Assignees

• Ppg Ind Ohio Inc

Inventors

• Puodziukynaite Egle
• Wilson Craig A
• Stone David
• Serene James C
• Steely Lee B

Classifications

• C09D5/4465

  Polyurethanes · CPC title

• C09D5/4407

  with polymers obtained by polymerisation reactions involving only carbon-to-carbon unsaturated bonds · CPC title

• C09D7/63

  organic · CPC title

• C09D5/4453 Primary

  characterised by the nature of the curing agent · CPC title

• C09D175/02

  Polyureas · CPC title