Liquid coating compositions that include a compound formed from at least one polyfunctional isocyanurate, related multi-layer composite coatings, methods and coated substrates

• US 20060089452A1
• Filed: 10/27/2004
• Published: 04/27/2006
• Est. Priority Date: 10/27/2004
• Status: Abandoned Application

• Current Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Inventors: Ambrose, Ronald R., Retsch, William H. Jr., Schneider, John R.
• Application Number:
  US10/974,235
• Publication Number:
  US 20060089452A1
• Time in Patent Office: Days
• US Class Current: 524/589
• CPC Class Codes: C08K 3/22 of metals
• CPC Class Codes: C08K 3/36 Silica
• CPC Class Codes: C08K 5/098 Metal salts of carboxylic acids
• CPC Class Codes: C08K 5/29 Compounds containing one or more carbon-to-nitrogen double bonds
• CPC Class Codes: C08K 5/34924 containing cyanurate groups; Tautomers thereof
• CPC Class Codes: C08L 23/06 Polyethene
• CPC Class Codes: C08L 23/12 Polypropene
• CPC Class Codes: C08L 2666/04 Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• CPC Class Codes: C08L 2666/22 Macromolecular compounds not provided for in C08L2666/16 - C08L2666/20
• CPC Class Codes: C08L 27/18 Homopolymers or copolymers or tetrafluoroethene
• CPC Class Codes: C08L 61/24 with urea or thiourea
• CPC Class Codes: C08L 63/06 Triglycidylisocyanurates
• CPC Class Codes: C08L 91/06 Waxes
• CPC Class Codes: C09D 167/00 Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain based on polyester-amides C09D177/12; based on polyester-imides C09D179/08; Coating compositions based on derivatives of such polymers
• CPC Class Codes: C09D 7/42 Gloss-reducing agents

Abstract

Liquid coating compositions are disclosed that include (a) at least one film forming resin, (b) at least one flatting agent, and (c) at least on compound formed from a polyfunctional isocyanurate. Also disclosed are methods for coating a substrate with such compositions, multi-layer composite coatings wherein at least one layer is deposited from such compositions, and substrates at least partially coated with such compositions. Methods for enhancing the flatting capability of at least one flatting agent in a liquid coating composition are also disclosed.

Claims

1. A liquid coating composition comprising:

(a) at least one film-forming resin;

(b) at least one flatting agent; and

(c) at least one compound formed from at least one polyfunctional isocyanurate,

wherein the at least one compound formed from at least one polyfunctional isocyanurate is present in the composition in an amount sufficient to result in a coating having a 60°

gloss that is at least 10% lower compared to a coating deposited at similar conditions from a similar liquid coating composition that does not include the at least one compound formed from at least one polyfunctional isocyanurate.

2. The liquid coating composition of claim 1, wherein the at least one film-forming resin comprises at least one thermosetting film-forming resin.

3. The liquid coating composition of claim 2, wherein the at least one film-forming resin is formed from the reaction of at least one polymer having at least one type of reactive group and at least one curing agent having reactive groups reactive with the at least one type of reactive group of the at least one polymer.

4. The liquid coating composition of claim 1, wherein the at least one flatting agent comprises amorphous or pyrogenic silica, silica gels, alumina, titania, zirconia, zircon, tin oxide, magnesia, or a mixture thereof.

5. The liquid coating composition of claim 4, wherein the at least one flatting agent comprises silica.

6. The liquid coating composition of claim 4, wherein the at least one flatting agent comprises a synthetic amorphous silica gel.

7. The liquid coating composition of claim 1, wherein the at least one flatting agent comprises polypropylene, polyethylene, polytetrafluoroethylene, Al, Zn, Ca or Mg stearate, a micronised polypropylene wax, a urea-formaldehyde condensate, or a mixture thereof.

8. The liquid coating composition of claim 1, wherein the at least one polyfunctional isocyanurate comprises tris(hydroxyethyl) isocyanurate, triglycidyl isocyanurate, triallyl isocyanurate, the isocyanurate trimer of heaxmethylene diisocyanate, or a mixture thereof.

9. The liquid coating composition of claim 1, wherein the at least one compound formed from at least one polyfunctional isocyanurate is present in the liquid coating composition is an amount of 1 up to 50 weight percent, with weight percent being based on the total weight of resins solids in the composition.

10. The liquid coating composition of claim 1, wherein the at least one compound formed from at least one polyfunctional isocyanurate is present in the composition in an amount sufficient to result in a coating having a 60°

gloss that is at least 50% lower compared to a coating deposited at similar conditions from a similar liquid coating composition that does not include the at least one compound formed from at least one polyfunctional isocyanurate.

11. The liquid coating composition of claim 10, wherein the at least one compound formed from at least one polyfunctional isocyanurate is present in the composition in an amount sufficient to result in a coating having a 60°

gloss that is at least 75% lower compared to a coating deposited at similar conditions from a similar liquid coating composition that does not include the at least one compound formed from at least one polyfunctional isocyanurate.

12. The liquid coating composition of claim 1, wherein the liquid coating composition is a sprayable, high solids composition that is capable of producing a low gloss coating.

13. The liquid coating composition of claim 12, wherein the liquid coating composition comprises at least 50 weight percent total solids based on the total weight of the liquid coating composition.

14. The liquid coating composition of claim 1, wherein the at least one compound formed from at least one polyfunctional isocyanurate has a Hansen hydrogen bonding solubility parameter of no more than 6.5 (cal/cm³)^1/2.

15. The liquid coating composition of claim 14, wherein the at least one compound formed from at least one polyfunctional isocyanurate has a Hansen hydrogen bonding solubility parameter of no more than 6.0 (cal/cm³)^1/2.

16. The liquid coating composition of claim 15, wherein the at least one compound formed from at least one polyfunctional isocyanurate has a Hansen hydrogen bonding solubility parameter of no more than 4.0 (cal/cm³)^1/2.

17. The liquid coating composition of claim 1, wherein the at least one compound formed from a polyfunctional isocyanurate comprises the reaction product of reactants comprising:

(i) at least one polyfunctional isocyanurate, and (ii) at least one long chain monofunctional reactant having a reactive group reactive with the reactive groups of the at least one polyfunctional isocyanurate.

18. The liquid coating composition of claim 17, wherein the at least one long chain monofunctional reactant comprises at least 18 carbon atoms.

19. The liquid coating composition of claim 17, wherein the at least one compound formed from at least one polyfunctional isocyanurate comprises the reaction product of reactants further comprising:

(iii) at least one polyfunctional reactant having at least two reactive groups reactive with the reactive groups of the at least one polyfunctional isocyanurate.

20. The liquid coating composition of claim 3, wherein the at least one compound formed from at least one polyfunctional isocyanurate comprises the reaction product of reactants comprising:

(i) at least one polyfunctional isocyanurate, (ii) at least one long chain monofunctional reactant having a reactive group reactive with the reactive groups of the at least one polyfunctional isocyanurate (iii) at least one polyfunctional reactant having at least two reactive groups reactive with the reactive groups of the at least one polyfunctional isocyanurate, and (iv) at least one reactant comprising at least one reactive group reactive with the reactive groups of the at least one polyfunctional isocyanurate and at least one reactive group reactive with the reactive groups of the at least one curing agent.

21. The liquid coating composition of claim 1, wherein the at least one compound formed from a polyfunctional isocyanurate comprises a polymer having a Mw of from 1,500 to 10,000.

22. The liquid coating composition of claim 1, wherein the at least one compound formed from a polyfunctional isocyanurate comprises a polymer having a Mw/Mn of from 1.5 to 3.0.

23. The liquid coating composition of claim 1, wherein the at least one polyfunctional isocyanurate comprises three epoxide groups.

24. A substrate at least partially coated with a coating deposited a composition comprising the liquid coating composition of claim 1.

25. A multi-layer composite coating wherein at least one layer of the multi-layer composite coating is deposited from a composition comprising the liquid coating composition of claim 1.

26. A method of coating a substrate comprising:

(a) applying a composition comprising the liquid coating composition of claim 1 to at least a portion of the substrate,

(b) coalescing the liquid coating composition over the substrate in the form of a substantially continuous film, and

(c) curing the liquid coating composition.

27. A liquid coating composition comprising:

(a) at least one film-forming resin;

(b) at least one flatting agent; and

(c) at least one compound formed from at least one polyfunctional isocyanurate,

wherein the at least one compound formed from at least one polyfunctional isocyanurate has a Hansen hydrogen bonding solubility parameter of no more than 6.5 (cal/cm³)^1/2.

28. The liquid coating composition of claim 27, wherein the at least one film-forming resin comprises at least one thermosetting film-forming resin formed from the reaction of at least one polymer having at least one type of reactive group and at least one curing agent having reactive groups reactive with the at least one type of reactive group of the at least one polymer.

29. The liquid coating composition of claim 27, wherein the at least one flatting agent comprises amorphous or pyrogenic silica, silica gels, alumina, titania, zirconia, zircon, tin oxide, magnesia, or a mixture thereof.

30. The liquid coating composition of claim 29, wherein the at least one flatting agent comprises silica.

31. The liquid coating composition of claim 30, wherein the at least one flatting agent comprises a synthetic amorphous silica gel.

32. The liquid coating composition of claim 27, wherein the at least one flatting agent comprises polypropylene, polyethylene, polytetrafluoroethylene, Al, Zn, Ca or Mg stearate, a micronised polypropylene wax, a urea-formaldehyde condensate, or a mixture thereof.

33. The liquid coating composition of claim 27, wherein the at least one polyfunctional isocyanurate comprises tris(hydroxyethyl) isocyanurate, triglycidyl isocyanurate, triallyl isocyanurate, the isocyanurate trimer of heaxmethylene diisocyanate, or a mixture thereof.

34. The liquid coating composition of claim 27, wherein the at least one compound formed from at least one polyfunctional isocyanurate is present in the composition in an amount sufficient to result in a coating having a 60°

gloss that is at least 50% lower compared to a coating deposited at similar conditions from a similar liquid coating composition that does not include the at least one compound formed from at least one polyfunctional isocyanurate.

35. The liquid coating composition of claim 27, wherein the composition is a sprayable, high solids composition that is capable of producing a low gloss coating.

36. The liquid coating composition of claim 27, wherein the at least one compound formed from at least one polyfunctional isocyanurate has a Hansen hydrogen bonding solubility parameter of no more than 6.0 (cal/cm³)^1/2.

37. The liquid coating composition of claim 36, wherein the at least one compound formed from at least one polyfunctional isocyanurate has a Hansen hydrogen bonding solubility parameter of no more than 4.0 (cal/cm³)^1/2.

38. The liquid coating composition of claim 27, wherein the at least one compound formed from at least one polyfunctional isocyanurate comprises the reaction product of reactants comprising:

(i) at least one polyfunctional isocyanurate, and (ii) at least one long chain monofunctional reactant having a reactive group reactive with the reactive groups of the at least one polyfunctional isocyanurate.

39. The liquid coating composition of claim 38, wherein the at least one long chain monofunctional reactant comprises at least 18 carbon atoms.

40. The liquid coating composition of claim 38, wherein the at least one compound formed from at least one polyfunctional isocyanurate comprises the reaction product of reactants further comprising:

(iii) at least one polyfunctional reactant having at least two reactive groups reactive with the reactive groups of the at least one polyfunctional isocyanurate.

41. The liquid coating composition of claim 28, wherein the at least one compound formed from at least one polyfunctional isocyanurate comprises the reaction product of reactants comprising:

(i) at least one polyfunctional isocyanurate, and (ii) at least one long chain monofunctional reactant having a reactive group reactive with the reactive groups of the at least one polyfunctional isocyanurate (iii) at least one polyfunctional reactant having at least two reactive groups reactive with the reactive groups of the at least one polyfunctional isocyanurate, and (iv) at least one reactant comprising at least one reactive group reactive with the reactive groups of the at least one polyfunctional isocyanurate and at least one reactive group reactive with the reactive groups of the at least one curing agent.

42. A substrate at least partially coated with a coating deposited a composition comprising the liquid coating composition of claim 27.

43. A multi-layer composite coating wherein at least one layer of the multi-layer composite coating is deposited from a composition comprising the liquid coating composition of claim 27.

44. A method of coating a substrate comprising:

(a) applying a composition comprising the liquid coating composition of claim 27 to at least a portion of the substrate,

(b) coalescing the liquid coating composition over the substrate in the form of a substantially continuous film, and

(c) curing the liquid coating composition.

45. A liquid coating composition comprising:

(a) at least one film-forming resin;

(b) at least one flatting agent; and

(c) at least one compound formed from at least one polyfunctional isocyanurate,

wherein the liquid coating composition is;

(i) capable of producing a low gloss coating,

(ii) a high solids composition, and

(iii) sprayable.

46. The liquid coating composition of claim 45, wherein the composition is capable of producing a low gloss coating when applied at film thicknesses of up to 20 mils.

47. The liquid coating composition of claim 45, wherein the at least one film-forming resin comprises at least one thermosetting film-forming resin formed from the reaction of at least one polymer having at least one type of reactive group and at least one curing agent having reactive groups reactive with the at least one type of reactive group of the at least one polymer.

48. The liquid coating composition of claim 45, wherein the at least one flatting agent comprises amorphous or pyrogenic silica, silica gels, alumina, titania, zirconia, zircon, tin oxide, magnesia, or a mixture thereof.

49. The liquid coating composition of claim 48, wherein the at least one flatting agent comprises silica.

50. The liquid coating composition of claim 49, wherein the at least one flatting agent comprises a synthetic amorphous silica gel.

51. The liquid coating composition of claim 45, wherein the at least one flatting agent comprises polypropylene, polyethylene, polytetrafluoroethylene, Al, Zn, Ca or Mg stearate, a micronised polypropylene wax, a urea-formaldehyde condensate, or a mixture thereof.

52. The liquid coating composition of claim 45, wherein the at least one polyfunctional isocyanurate comprises tris(hydroxyethyl) isocyanurate, triglycidyl isocyanurate, triallyl isocyanurate, the isocyanurate trimer of heaxmethylene diisocyanate, or a mixture thereof.

53. The liquid coating composition of claim 45, wherein the at least one compound formed from at least one polyfunctional isocyanurate has a Hansen hydrogen bonding solubility parameter of no more than 6.5 (cal/cm³)^1/2.

54. The liquid coating composition of claim 53, wherein the at least one compound formed from at least one polyfunctional isocyanurate has a Hansen hydrogen bonding solubility parameter of no more than 6.0.(cal/cm³)^1/2.

55. The liquid coating composition of claim 45, wherein the at least one compound formed from at least one polyfunctional isocyanurate comprises the reaction product of reactants comprising:

(i) at least one polyfunctional isocyanurate, and (ii) at least one long chain monofunctional reactant having a reactive group reactive with the reactive groups of the at least one polyfunctional isocyanurate.

56. The liquid coating composition of claim 55, wherein the at least one long chain monofunctional reactant comprises at least 18 carbon atoms.

57. The liquid coating composition of claim 55, wherein the at least one compound formed from at least one polyfunctional isocyanurate comprises the reaction product of reactants further comprising:

(iii) at least one polyfunctional reactant having at least two reactive groups reactive with the reactive groups of the at least one polyfunctional isocyanurate.

58. The liquid coating composition of claim 47, wherein the at least one compound formed from at least one polyfunctional isocyanurate comprises the reaction product of reactants comprising:

(i) at least one polyfunctional isocyanurate, and (ii) at least one long chain monofunctional reactant having a reactive group reactive with the reactive groups of the at least one polyfunctional isocyanurate (iii) at least one polyfunctional reactant having at least two reactive groups reactive with the reactive groups of the at least one polyfunctional isocyanurate, and (iv) at least one reactant comprising at least one reactive group reactive with the reactive groups of the at least one polyfunctional isocyanurate and at least one reactive group reactive with the reactive groups of the at least one curing agent.

59. A substrate at least partially coated with a coating deposited a composition comprising the liquid coating composition of claim 45.

60. A multi-layer composite coating wherein at least one layer of the multi-layer composite coating is deposited from a composition comprising the liquid coating composition of claim 45.

61. A method of coating a substrate comprising:

(a) applying a composition comprising the liquid coating composition of claim 45 to at least a portion of the substrate,

(b) coalescing the liquid coating composition over the substrate in the form of a substantially continuous film, and

(c) curing the liquid coating composition.

62. A liquid coating composition comprising:

(a) at least one film-forming resin;

(b) at least one flatting agent; and

(c) at least one compound comprising the reaction product of reactants comprising;

(i) at least one polyfunctional isocyanurate, and

(ii) at least one long chain monofunctional reactant comprising a reactive group reactive with the reactive groups of the at least one polyfunctional isocyanurate.

63. The liquid coating composition of claim 62, wherein the at least one film-forming resin comprises at least one thermosetting film-forming resin formed from the reaction of at least one polymer having at least one type of reactive group and at least one curing agent having reactive groups reactive with the at least one type of reactive group of the at least one polymer.

64. The liquid coating composition of claim 62, wherein the at least one flatting agent comprises amorphous or pyrogenic silica, silica gels, alumina, titania, zirconia, zircon, tin oxide, magnesia, or a mixture thereof.

65. The liquid coating composition of claim 64, wherein the at least one flatting agent comprises silica.

66. The liquid coating composition of claim 65, wherein the at least one flatting agent comprises a synthetic amorphous silica gel.

67. The liquid coating composition of claim 62, wherein the at least one flatting agent comprises polypropylene, polyethylene, polytetrafluoroethylene, Al, Zn, Ca or Mg stearate, a micronised polypropylene wax, a urea-formaldehyde condensate, or a mixture thereof.

68. The liquid coating composition of claim 62, wherein the at least one polyfunctional isocyanurate comprises tris(hydroxyethyl) isocyanurate, triglycidyl isocyanurate, triallyl isocyanurate, the isocyanurate trimer of heaxmethylene diisocyanate, or a mixture thereof.

69. The liquid coating composition of claim 62, wherein the at least one compound (c) has a Hansen hydrogen bonding solubility parameter of no more than 6.5 (cal/cm³)^1/2.

70. The liquid coating composition of claim 69, wherein the at least one compound (c) has a Hansen hydrogen bonding solubility parameter of no more than 6.0 (cal/cm³)^1/2.

71. The liquid coating composition of claim 62, wherein the at least one long chain monofunctional reactant comprises at least 18 carbon atoms.

72. The liquid coating composition of claim 62, wherein the at least one compound (c) comprises the reaction product of reactants further comprising:

(iii) at least one polyfunctional reactant having at least two reactive groups reactive with the reactive groups of the at least one polyfunctional isocyanurate.

73. The liquid coating composition of claim 63, wherein the at least one compound (c) comprises the reaction product of reactants comprising:

(i) at least one polyfunctional isocyanurate, and (ii) at least one long chain monofunctional reactant having a reactive group reactive with the reactive groups of the at least one polyfunctional isocyanurate (iii) at least one polyfunctional reactant having at least two reactive groups reactive with the reactive groups of the at least one polyfunctional isocyanurate, and (iv) at least one reactant comprising at least one reactive group reactive with the reactive groups of the at least one polyfunctional isocyanurate and at least one reactive group reactive with the reactive groups of the at least one curing agent.

74. A substrate at least partially coated with a coating deposited a composition comprising the liquid coating composition of claim 62.

75. A multi-layer composite coating wherein at least one layer of the multi-layer composite coating is deposited from a composition comprising the liquid coating composition of claim 62.

76. A method of coating a substrate comprising:

(a) applying a composition comprising the liquid coating composition of claim 62 to at least a portion of the substrate,

(b) coalescing the liquid coating composition over the substrate in the form of a substantially continuous film, and

(c) curing the liquid coating composition.

77. A coating deposited on at least a portion of a substrate, wherein the coating is deposited from a composition comprising a sprayable, high solids liquid coating composition comprising:

(a) at least one film-forming resin;

(b) at least one flatting agent; and

(c) at least one compound formed from an isocyanurate,

wherein the coating is a low gloss coating.

78. A method for enhancing the flatting capability of at least one flatting agent in a liquid coating composition comprising at least one film-forming resin and at least one flatting agent, the method comprising the step of including in the composition at least one compound formed from at least one polyfunctional isocyanurate.