RESINS, LOW TEMPERATURE FORMULATIONS, AND COATINGS DERIVED THEREFROM

• US 20090105377A1
• Filed: 03/20/2006
• Published: 04/23/2009
• Est. Priority Date: 03/18/2005
• Status: Active Grant

• Current Assignee: Battelle Memorial Institute
• Original Assignee: Battelle Memorial Institute
• Inventors: Cafmeyer, Jeffrey T., King, Jerry L II, Vijayendran, Bhima R., Mitchell, Katherine P., Clingerman, Michael C.
• Granted Patent: US 8,106,148 B2
• Time in Patent Office: Days
• US Class Current: 524/88
• CPC Class Codes: C08G 63/672 Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C08K 3/013 Fillers, pigments or reinforcing additives
• CPC Class Codes: C08K 5/0041 Optical brightening agents, organic pigments
• CPC Class Codes: C08L 2205/18 Spheres
• CPC Class Codes: C08L 25/14 with unsaturated esters
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 2666/06 Homopolymers or copolymers of unsaturated hydrocarbons; Derivatives thereof
• CPC Class Codes: C08L 67/025 containing polyether sequences
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C08L 89/00 Compositions of proteins; Compositions of derivatives thereof foodstuff preparations A23J3/00
• CPC Class Codes: G03G 9/08755 Polyesters
• CPC Class Codes: G03G 9/08759 Polyethers
• CPC Class Codes: G03G 9/08764 Polyureas; Polyurethanes
• CPC Class Codes: G03G 9/08775 Natural macromolecular compounds or derivatives thereof
• CPC Class Codes: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]
• CPC Class Codes: Y10T 428/31794 Of cross-linked polyester

Abstract

A series of resins were synthesized using a range of bio-based materials to control the molecular architecture, and therefore the properties, of the inventive resins. The utility of these resins was demonstrated in the formulation of powder coatings, such as β-hydroxy amide crosslinked and hybrid types. Generally, the bio-based resins flowed out on heating faster than conventional petrochemically-based resins, allowing the use of lower temperatures in the curing oven than is typically possible and a more active catalyst system, especially in the carboxylic acid-epoxy crosslinked hybrid coatings formulations.

Claims

1. (canceled)

2. (canceled)

3. (canceled)

4. A carboxyl or hydroxyl functional polyester coating resin comprising:

the reaction product of

A. a dianhydrohexitol;

B. a fatty dimer diol and/or a fatty dimer diacid;

C. a cyclic diacid, cyclic diester, or cyclic diacid chloride that contribute rigidifying effects; and

D. a catalyst;

wherein the carboxyl or hydroxyl functional coating resin has a Tg between about 40°

C. and 80°

C.

5. The polyester resin according to claim 4, further comprising an optional diol that is not ethylene glycol.

6. The resin according to claim 4, comprising an optional second diacid, diester, or diacid chloride.

7. The resin according to claim 4, wherein the dianhydrohexitol comprises an isosorbide.

10. A powder coating formulation comprising

the reaction product of

A. the resin of claim 4; and

B. a crosslinker

11. The powder formulation according to claim 10 wherein the crosslinker has epoxy functionality.

12. The powder formulation according to claim 10 wherein the crosslinker has β

-hydroxy amide functionality.

13. A powder coating comprising:

A. a substrate;

B. a cured powder on the substrate, wherein the cured powder is the reaction product of

a. the resin of claim 4; and

b. a crosslinker.

14. The powder coating according to claim 13 wherein the crosslinker has epoxy functionality.

15. The powder coating according to claim 13 wherein the crosslinker has β

-hydroxy amide functionality.

16. The powder coating according to claim 13, wherein the powder coating provides a class A finish.

17. The powder coating according to claim 13, wherein the substrate is temperature sensitive.

42. The coating resin according to claim 4, wherein the coating resin has a Tg above about 50°

C.

8. (canceled)

9. (canceled)

18. (canceled)

19. (canceled)

20. A method for making a carboxyl or hydroxyl functional polyester coating resin comprising:

a, selecting a tough, crystalline bio-based monomer of a dianhydrohexitol;

b. co-reacting with a fatty dimer diol and/or a fatty dimer diacid; and

a cyclic diacid, cyclic diester, or cyclic diacid chloride that contributes rigidifying effects;

to form resins comprising;

a Tg of greater than about 40°

C. and less than about 80°

C.

22. The method of claim 20 wherein the resins have excess unsaturation that is available for secondary curing mechanism.

23. The method of claim 20 wherein the resins of claim 20 are formulated into coatings compositions utilizing a β

-hydroxy amide transesterification cure;

that is the reaction of a β

-hydroxyl amide curative reacting with a carboxyl group of a polyester acid resin.

43. The coating resin according to claim 20, wherein the coating resin has a Tg above about 50°

C.

21. (canceled)

24. (canceled)

25. (canceled)

26. (canceled)

27. (canceled)

28. (canceled)

29. (canceled)

30. (canceled)

31. (canceled)

32. (canceled)

33. (canceled)

34. (canceled)

35. A powder coating comprising:

A. a carboxyl or hydroxyl functional coating resin comprising;

the reaction product of

a. a dianhydrohexitol;

b. a fatty dimer acid and/or a fatty dimer diol;

c. a cyclic diacid, cyclic diester, or cyclic diacid chloride that contributes rigidifying effects;

wherein the carboxyl or hydroxyl functional coating resin has a Tg between about 40°

C. and 80°

C.;

B. a crosslinker; and

C. an optional pigment.

36. The powder coating according to claim 35, comprising a catalyst for the reaction.

37. The powder according to claim 35, comprising a pigment dispersion aid.

38. The powder coating according to claim 35, comprising:

when the resin has a carboxyl group, reacting the carboxyl group of the carboxy functionality with either a β

-hydroxyl amide in a self catalyzed trans-esterification reaction or with a polyepoxy functional polymer.

39. The powder coating according to claim 35, comprising:

when the resin has a hydroxyl functional group, reacting the hydroxyl group of the hydroxyl functionality with an epoxy functional acrylic.

40. The powder coating according to claim 35, comprising optional excipients.

44. The coating resin according to claim 35, wherein the coating resin has a Tg above about 50°

C.

41. All novel and nonobvious compositions, methods and uses disclosed herein.