Curable compositions comprising acetoacetoxy and imine functionality

• US 6,297,320 B1
• Filed: 11/11/1999
• Issued: 10/02/2001
• Est. Priority Date: 11/20/1998
• Status: Expired due to Term

• Current Assignee: Sherwin-Williams Company
• Original Assignee: Sherwin-Williams Company
• Inventors: Tang, Weilin, DʼErrico, Michael J., Leonard, David P., Ding, Hong
• Primary Examiner(s): Wilson, Donald R.
• Application Number:
  US09/438,821
• Time in Patent Office: 691 Days
• Field of Search: 525/107, 525/111, 525/113, 525/153, 525/154, 525/155, 525/157, 525/159, 525/330.5, 525/342, 525/374, 525/379
• US Class Current: 525/107
• CPC Class Codes: C08F 20/00 Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
• CPC Class Codes: C08F 8/30 Introducing nitrogen atoms or nitrogen-containing groups
• CPC Class Codes: C08L 2666/28 Non-macromolecular organic substances
• CPC Class Codes: C09D 133/062 Copolymers with monomers not covered by C09D133/06

Abstract

A multi-component curable composition which is reactive upon admixing of the components and which comprises:

(i) an acrylic polymer having acetoacetoxy functionality; and

(ii) an acetoacetoxy functional derivative of a low molecular weight polyol; and

(iii) a crosslinking component comprising at least one imine functional compound having an average of at least two imine groups per molecule which are reactive with acetoacetoxy functionality.

Claims

1. A multi-component curable composition which is reactive upon admixing of the components and which consisting essentially of:

(i) an acrylic polymer having acetoacetoxy functionality; and

(ii) an acetoacetoxy functional derivative of a low molecular weight polyol wherein the low molecular weight polyol has a number average molecular weight less than about 1000; and

(iii) a crosslinking component comprising at least one imine functional compound having an average of at least two imine groups per molecule which are reactive with acetoacetoxy functionality.

2. The curable composition of claim 1 wherein the curable composition also comprises an amine functional compound having an average of at least two primary amine groups per molecule.

3. The composition of claim 1 wherein the imine functional compound is an adduct obtained by the reaction of:

(i) an imine having at least one hydroxyl or amine group with

(ii) one or more compounds having epoxy or isocyanate functionality which is reactive with the hydroxyl or amine group.

4. The composition of claim 1 wherein the composition also includes an organosilane.

5. The composition of claim 4 wherein the organosilane is an epoxy functional organosilane.

6. The composition of claim 4 wherein the organosilane is an amine functional organosilane.

7. The composition of claim 3 wherein the epoxy functional compound is selected from the group consisting of mono epoxies, novalac epoxies, cycloaliphatic epoxies, Bisphenol A epoxies, and mixtures thereof.

8. The composition of claim 3 wherein the imine crosslinker comprises the reaction products of an imine having at least one primary or secondary amine group with a monoepoxy.

9. The composition of claim 3 wherein the imine crosslinker comprises the reaction product of an imine having at least one primary or secondary amine group and a polyepoxide having an average of at least two epoxy groups per molecule.

10. The composition of claim 3 wherein the imine crosslinker comprises the reaction product of an imine having at least one primary or secondary amine group and a monoepoxide and the reaction product of an imine having at least one primary or secondary amine group and a polyepoxide having an average of at least two epoxy groups per molecule.

11. The reactive composition of claim 1 wherein the equivalent ratio of imine functionality to acetoacetoxy functionality is at least 1.01 to 1.0.

12. The reactive composition of claim 2 wherein the equivalent ratio of amine and imine functionality to acetoacetoxy functionality is at least 1.01 to 1.

13. The curable composition of claim 1 wherein the acrylic polymer is obtained by the polymerization of a monomer mixture comprising from 10 to about 75% by weight of an acetoacetoxy functional unsaturated monomer.

14. The curable composition of claim 13 wherein the acrylic polymer is obtained by the polymerization of a monomer mixture comprising from 25 to about 50% by weight of an acetoacetoxy functional unsaturated monomer.

15. The curable composition of claim 1 wherein the acrylic polymer having acetoacetoxy functionality is obtained by converting a hydroxy functional acrylic polymer to an acetoacetoxy functional polymer.

16. The curable composition of claim 1 wherein at least 1% of the total equivalents of acetoacetoxy functionality are provided by the acetoacetoxy functional polyol derivative.

17. The curable composition of claim 1 wherein 10 to 80% of the total equivalents of acetoacetoxy functionality are provided by the acetoacetoxy functional polyol derivative.

18. The curable composition of claim 1 wherein the low molecular weight polyol is selected from the group of aliphatic, polyester, polyether and polyurethane polyols.

19. The curable composition of claim 1 wherein the low molecular weight polyol has a number average molecular weight less than about 500.

20. The curable composition of claim 1 wherein the acrylic polymer having acetoacetoxy functionality has a number average molecular weight of at least 1,000.

21. The curable composition of claim 1 wherein the acrylic polymer having acetoacetoxy functionality has a number average molecular weight less than 20,000.

22. The curable composition of claim 1 wherein the acrylic polymer having acetoacetoxy functionality has a number average molecular weight less than 10,000.

23. The composition of claim 3 wherein the imine having at least one amine group is the reaction product of ethylene triamine and an aldehyde or ketone.

24. The composition of claim 1 wherein the composition also comprises a polyepoxide.

25. The composition of claim 2 wherein the composition also comprises a polyepoxide.

26. The composition of claim 1 wherein the composition is non-aqueous.

27. A multi-component curable composition which is reactive upon admixing of the components which consisting essentially of:

(i) an acrylic polymer having acetoacetoxy functionality and a number average molecular weight of at least about 1,000; and

(ii) an acetoacetoxy functional derivative of a low molecular weight polyol wherein the low molecular weight polyol has a number average molecular weight less than about 1,000; and

(iii) at least one imine functional compound having an average of at least two imine groups per molecule which are reactive with acetoacetoxy functionality; and

(iv) at least one amine functional compound having an average of at least two primary amine groups per molecule.

28. The composition of claim 27 wherein the low molecular weight polyol has a number average molecular weight less than 500.

29. The composition of claim 27 wherein the imine functional compound comprises the reaction product of:

(i) an imine having at least two imine groups and at least one reactive group other than an imine; and

(ii) a compound having one or more chemical groups capable of reaction with the reactive group.

30. The composition of claim 27 wherein the imine functional compound comprises the reaction product of an imine having at least one primary or secondary amine group and a monoepoxide and the reaction product of an imine having at least one primary or secondary amine group and a polyepoxide having an average of at least two epoxy groups per molecule.

31. A multi-component curable composition which is reactive upon admixing of the components which comprises:

(i) at least one acetoacetoxy functional compound having an average of at least two acetoacetoxy groups per molecule; and

(ii) an imine functional compound having an average of at least two imine groups per molecule and which comprises the reaction product of an imine having at least one primary or secondary amine group and a polyepoxide; and

(iii) an imine functional compound having an average of at least two imine groups per molecule and which comprises the reaction product of an imine having at least one primary or secondary amine group and a monoepoxide.

32. The composition of claim 31 wherein the acetoacetoxy functional compound comprises an acrylic polymer having acetoacetoxy functionality.

33. The composition of claim 31 wherein the acetoacetoxy functional compound comprises an acetoacetoxy functional derivative of a low molecular weight polyol wherein the low molecular weight polyol has a number average molecular weight less than about 1000.

34. The composition of claim 31 wherein the composition also comprises an organosilane.

35. The composition of claim 31 wherein the composition also comprises an amine functional compound having an average of at least two primary amine groups per molecule.

36. The composition of claim 31 wherein the composition also comprises a polyepoxide.