Curable Film-Forming Compositions Demonstrating Decreased Cure Time with Stable Pot Life

Patent metadata

Field	Value
Publication number	US-2022010165-A1
Application number	US-201817292413-A
Country	US
Kind code	A1
Filing date	Nov 8, 2018
Priority date	Nov 8, 2018
Publication date	Jan 13, 2022
Grant date	—

Abstract

The present invention is directed to an aqueous curable film-forming composition comprising: (a) a film-forming component comprising an aliphatic di- or higher functional polyisocyanate; and (b) a catalyst additive comprising: (i) a catalytic organic compound comprising iron (II) and optionally tin; and (ii) a beta-diketone. The present invention is further directed to a method of controlling the rate of cure of an aqueous curable film-forming composition. The method comprises adding to the aqueous curable film-forming composition the catalyst additive described above; the aqueous curable film-forming composition comprises a film-forming component comprising an aliphatic di- or higher functional polyisocyanate. The present invention is additionally directed to a coated article comprising a cured coating layer applied on at least one surface of a substrate to form a coated substrate; wherein the cured coating layer is deposited from the aqueous curable film-forming composition described above.

First claim

Therefore, we claim:

1 . A curable, aqueous film-forming composition comprising:
(a) a film-forming component comprising an aliphatic di- or higher functional polyisocyanate; and (b) a catalyst additive comprising:
(i) a catalytic organic compound comprising iron (II) and optionally tin; and
(ii) a beta-diketone.

2 . The curable film-forming composition of claim 1 , wherein the polyisocyanate has an average isocyanate functionality greater than two.

3 . The curable film-forming composition of claim 1 , wherein the film-forming component (a) further comprises a film-forming polymer that is different from the polyisocyanate, comprising functional groups reactive with isocyanate functional groups in the polyisocyanate.

4 . The curable film-forming composition of claim 3 , wherein the film-forming polymer comprises an acrylic polymeric polyol, a polyether polymeric polyol, and/or a polyester polymeric polyol.

5 . The curable film-forming composition of claim 3 , wherein the equivalent ratio of isocyanate groups in the polyisocyanate to the reactive functional groups in the film-forming polymer is higher than 2:1.

6 . The curable film-forming composition of claim 5 , wherein the equivalent ratio of isocyanate groups in the polyisocyanate to the reactive functional groups in the film-forming polymer is at least 5:1.

7 . The curable film-forming composition of claim 1 , wherein the catalyst additive (b) further comprises (iii) a tertiary amine.

8 . The curable film-forming composition of claim 7 , wherein the tertiary amine (iii) comprises dimethylcyclohexylamine, diethylcyclohexylamine, dimethylethanolamine, a dimethylethanolamine ether, N-methylpiperidine, 1,4-diazabicyclo[2.2.2]octane, and/or triethylamine.

9 . The curable film-forming composition of claim 7 , wherein the molar ratio of catalytic organic compound (i) to tertiary amine (iii) ranges from 0.05 to 0.10.

10 . The curable film-forming composition of claim 1 , wherein the catalytic organic compound (i) comprises one or more of: an iron (II) complex of 2-(dimethylamino)benzoic acid, an iron (II) complex of dimethyl [2,2′-bipyridine]-6-6′dicarboxylate, an iron (II) complex of 2-2′-bipyridine-6-6′-dicarboxylic acid, ferrous acetylacetonate, iron (II) oxalate hexahydrate, and iron (II) acetate.

11 . The curable film-forming composition of claim 1 , wherein the catalytic organic compound (i) is present in the curable film-forming composition in an amount of 0.10 to 0.8 percent by weight, based on the total weight of resin solids in the curable film-forming composition.

12 . The curable film-forming composition of claim 1 , wherein the beta-diketone (ii) comprises 2,4-pentanedione and/or 3-methyl-2,4-pentanedione.

13 . The curable film-forming composition of claim 1 , wherein the beta-diketone (ii) is present in the curable film-forming composition in an amount of 4 to 50 percent by weight, based on the total weight of resin solids in the curable film-forming composition.

14 . The curable film-forming composition of claim 3 , wherein the composition is a two-package composition, and each component of the catalyst additive (b) is independently present with the polyisocyanate in a first package and/or with the film-forming polymer in a second package.

15 . A chemical agent resistant coating formed from the curable film-forming composition of claim 3 .

16 . A method of controlling the rate of cure of an aqueous curable film-forming composition, comprising adding to the aqueous curable film-forming composition a catalyst additive comprising:
(i) a catalytic organic compound comprising iron (II) and optionally tin; and (ii) a beta-diketone; wherein the aqueous curable film-forming composition comprises a film-forming component comprising an aliphatic di- or higher functional polyisocyanate.

17 . The method of claim 16 , wherein the film-forming component further comprises a polymer that is different from the polyisocyanate, comprising functional groups reactive with isocyanate functional groups in the polyisocyanate.

18 . The method of claim 16 , wherein the catalytic organic compound (i) comprises one or more of: an iron (II) complex of 2-(dimethylamino)benzoic acid, an iron (II) complex of dimethyl [2,2′-bipyridine]-6-6′dicarboxylate, an iron (II) complex of 2-2′-bipyridine-6-6′-dicarboxylic acid, ferrous acetylacetonate, iron (II) oxalate hexahydrate, and iron (II) acetate.

19 . The method of claim 16 , wherein the catalyst additive further comprises (iii) a tertiary amine.

20 . The method of claim 19 , wherein tertiary amine (iii) comprises dimethylcyclohexylamine, dimethylethanolamine, and/or dimethylethanolamine ether.

21 . The method of claim 16 , wherein the beta-diketone (ii) comprises 2,4-pentanedione and/or 3-methyl-2,4-pentanedione.

22 . A coated article comprising:
(A) a substrate having at least one coatable surface; and (B) a cured coating layer applied on at least one surface of the substrate to form a coated substrate; wherein the cured coating layer is prepared from the aqueous curable film-forming composition of claim 1 .

23 . The coated article of claim 22 , wherein a primer coating layer is applied to the surface of the substrate prior to the application of the aqueous curable film-forming composition.

24 . The coated article of claim 22 , wherein said coated article comprises an aircraft or military land vehicle.

25 . A coated article comprising:
(A) a substrate having at least one coatable surface; and (B) a cured coating layer applied on at least one surface of the substrate to form a coated substrate; wherein the cured coating layer is deposited from the aqueous curable film-forming composition of claim 3 .

26 . The coated article of claim 22 , wherein the aqueous curable film-forming composition is applied directly to the surface of the substrate.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Lukus Peter Alan
• Pawlik Michael J
• Bezer Silvia
• Zawacky Steven R
• Schillinger Diane Jean
• Esarey Samuel Logan

Classifications

• C08G18/73

  acyclic · CPC title

• C09D5/002

  Priming paints (C09D5/08 takes precedence) · CPC title

• C08G18/222

  metal compounds not provided for in groups C08G18/225 - C08G18/26 · CPC title

• C08G18/42

  Polycondensates having carboxylic or carbonic ester groups in the main chain · CPC title

• C09D175/04 Primary

  Polyurethanes · CPC title