METHOD OF CURING A COATING COMPOSITION COMPRISING A RADICAL CURABLE COMPOUND AND AN ORGANOBORANE-AMINE COMPLEX

• US 20120116013A1
• Filed: 06/22/2010
• Published: 05/10/2012
• Est. Priority Date: 06/26/2009
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: Gutowski, Keith E., Ohrbom, Walter H., Cranfill, David, Campbell, Donald H.
• Granted Patent: US 8,653,183 B2
• Time in Patent Office: Days
• US Class Current: 524/560
• CPC Class Codes: C08J 3/24 Crosslinking, e.g. vulcanising, of macromolecules mechanical aspects B29C35/00; crosslinking agents C08K
• CPC Class Codes: C08K 5/55 Boron-containing compounds C08K5/0091 takes precedence
• CPC Class Codes: C09D 133/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C09D 4/00 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

Abstract

A method of curing a coating composition and a method of forming a cured coating on an automobile component are provided. The coating composition comprises a radical polymerizable compound and an organoborane-amine complex having an organoborane initiator, an amine blocking agent, and water. The method of curing the coating composition comprises the steps of combining the organoborane-amine complex, the radical polymerizable compound, and water to form the coating composition. Carbon dioxide is introduced into the coating composition or into a composition including at least one of the organoborane-amine complex, the radical polymerizable compound, and water prior to forming the coating composition. Carbonic acid is formed in situ within the coating composition through reaction of the water and carbon dioxide. The organoborane-amine complex is de-complexed with the carbonic acid thereby separating the organoborane initiator and the amine blocking agent. The radical polymerizable compound is polymerized using the organoborane initiator in the presence of oxygen.

Claims

1-15. -15. (canceled)

16. A method of curing a coating composition comprising a radical polymerizable compound and an organoborane-amine complex having an organoborane initiator, an amine blocking agent, and water, said method comprising the steps of:

A. combining the organoborane-amine complex, the radical polymerizable compound, and water to form the coating composition;

B. introducing carbon dioxide into the coating composition or into a composition including at least one of the organoborane-amine complex, the radical polymerizable compound, and water prior to forming the coating composition, wherein the carbon dioxide is present in the coating composition in a molar ratio of at least 500;

1 with the amine blocking agent of the organoborane-amine complex to thereby form in situ carbonic acid in a predetermined amount based upon temperature of the coating composition and/or pressure of an atmosphere surrounding the coating composition;

C. decomplexing the organoborane-amine complex with the carbonic acid thereby separating the organoborane initiator and the amine blocking agent; and

D. polymerizing the radical polymerizable compound using the organoborane initiator in the presence of oxygen.

17. The method as set forth in claim 16, wherein the predetermined amount of carbonic acid is further defined as a molar ratio of at least 1:

1 of carbonic acid to the amine blocking agent of the organoborane-amine complex.

18. The method as set forth in claim 16, wherein the carbonic acid is formed at atmospheric pressure of about 1 atm and a temperature of from about −

78°

C. to about 30°

C.

19. The method as set forth in claim 16, wherein the in situ carbonic acid is formed in the predetermined amount within a period of less than or equal to 60 minutes.

20. The method as set forth in claim 16, wherein the step of introducing carbon dioxide is further defined as exposing the coating composition to a controlled gaseous atmosphere containing carbon dioxide present in a concentration greater than concentration of carbon dioxide in ambient atmospheric air.

21. The method as set forth in claim 16, wherein the step of introducing carbon dioxide is further defined as introducing supercritical carbon dioxide into the coating composition or into the composition including at least one of the organoborane-amine complex, the radical polymerizable compound, and the water prior to forming the coating composition.

22. The method as set forth in claim 16, wherein the step of introducing carbon dioxide is further defined as introducing solid carbon dioxide into the coating composition or into the composition including at least one of the organoborane-amine complex, the radical polymerizable compound, and the water prior to forming the coating composition.

23. The method as set forth in claim 16, wherein the step of introducing the carbon dioxide is further defined as spraying the carbon dioxide from a nozzle of an impingement spray gun.

24. The method as set forth in claim 16, further comprising the step of limiting an amount of oxygen present in the coating composition.

25. The method as set forth in claim 16, wherein the organoborane-amine complex has the following formula:

26. The method as set forth in claim 16, wherein the radical polymerizable compound is selected from the group consisting of unsaturated acrylic ester resins, functional acrylic ester monomers, and combinations thereof.

27. The method as set forth in claim 16, wherein the radical polymerizable compound is present in an amount of from 90 to 97 percent by weight based on the total weight of the coating composition and the organoborane-amine complex is present in an amount of from 2 to 5 percent by weight based on the total weight of the coating composition.

28. The method as set forth in claim 16, wherein the step of decomplexing the organoborane complex occurs in the absence of external heating of the reactive composition.

29. The method as set forth in claim 16, wherein step A) further comprises applying the coating composition onto an automobile component.

30. An automobile component including a cured coating formed thereon according to the method as set forth in claim 29.