Coating compositions and coatings formed therefrom

• US 6,605,359 B2
• Filed: 06/20/2001
• Issued: 08/12/2003
• Est. Priority Date: 11/23/1998
• Status: Expired due to Fees

• Current Assignee: Akzo Nobel N.V. (Nouryon BV)
• Original Assignee: Akzo Nobel N.V. (Nouryon BV)
• Inventors: Wong, Philip Titsum, Znidersic, Kenneth M., Shemancik, Robin Carol, Speight, Robert Dale, Robinson, Gregory Frantz
• Primary Examiner(s): Dawson, Robert
• Assistant Examiner(s): Robertson, Jeffrey B.
• Application Number:
  US09/885,737
• Publication Number:
  US 20020115763A1
• Time in Patent Office: 783 Days
• Field of Search: 106/287.1, 106/287.13, 106/287.16, 106/287.25, 106/287.3, 528/28, 528/34, 528/119, 528/288, 528/367, 528/422, 524/189, 524/261, 524/265, 524/269, 428/413, 428/447, 428/473.5, 428/474.4, 428/480, 428/500
• US Class Current: 428/447
• CPC Class Codes: C09D 201/025 containing nitrogen atoms
• CPC Class Codes: Y10T 428/31511 Of epoxy ether
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane
• CPC Class Codes: Y10T 428/31721 Of polyimide
• CPC Class Codes: Y10T 428/31725 Of polyamide
• CPC Class Codes: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]
• CPC Class Codes: Y10T 428/31855 Of addition polymer from unsaturated monomers

Abstract

Novel coating compositions containing a polymer, a hydrazide and a silane, methods of making and using such compositions and a substrate coated with such coating compositions.

Claims

1. A coating composition comprising:

a polymer having at least one reactive group;

a hydrazide; and

an organosilane treated pigment which is obtained in-situ during formation of the coating composition;

the coating composition containing substantially no isocyanate or formaldehyde.

2. A coating composition as in claim 1 wherein the polymer is an acrylic polymer, modified acrylic polymer, polyepoxide, polyester, polyurethane, polyamide, polyimide, polysiloxane, polycarbonate or a mixture thereof.

3. A coating composition as in claim 1 wherein the at least one reactive group is a carboxyl, hydroxyl, epoxy, amino, keto, silane, silanol, or amido group.

4. A coating composition as in claim 1 wherein the organosilane treated pigment is made using a silane of the formula:

wherein n=1 to 1000;

R is an optionally substituted hydrocarbon group containing from 1 to 20 carbon atoms;

R₁ is the same or different at each occurrence and is a moiety selected from the group consisting of halogen, hydrogen, alkoxy, hydroxy, amino and epoxy groups; and

R₂ can be the same or different at each occurrence and is R or R₁ as defined above.

5. A coating composition as in claim 4 wherein the R₁ in the formula of the silane is an amino or epoxy group.

6. A coating composition as in claim 1 wherein the organosilane treated pigment is made using a silane of the formula:

7. A coating composition as in claim 1 further comprising a solvent.

8. A coating composition as in claim 7 wherein the solvent is water.

9. A coating composition as in claim 1 wherein the polymer is a latex polymer.

10. A coating composition as in claim 1 wherein the hydrazide is adipic acid dihydrazide.

11. A coating composition as in claim 1 wherein the organosilane treated pigment is obtained using an epoxy silane in the presence of a diamino silane.

12. A method of coating comprising

providing a composition containing a polymer, a hydrazide and an organosilane treated pigment which is obtained in-situ during formation of the coating composition, the polymer having at least one reactive group;

and

applying the composition to a substrate;

the coating composition containing substantially no isocyanate or formaldehyde.

13. A method as in claim 12 wherein the polymer is an acrylic polymer, modified acrylic polymer, polyepoxide, polyurethane, polyamide, polyimide, polysiloxane, polycarbonate or mixture thereof.

14. A method as in claim 12 wherein the at least one reactive group is a carboxyl, hydroxyl, epoxy, amino, keto, silane, silanol, amido group.

15. A method as in claim 12 wherein the organosilane treated pigment is made using a silane of the formula:

wherein n=1 to 1000;

R is an optionally substituted hydrocarbon group containing from 1 to 20 carbon atoms;

R₁ is the same or different at each occurrence and is a moiety selected from the group consisting of halogen, hydrogen, alkoxy, hydroxy, amino and epoxy groups; and

R₂ can be the same or different at each occurrence and is R or R₁ as defined above.

16. A method as in claim 15 wherein the R₁ in the formula of the silane is an amino or epoxy group.

17. A method as in claim 12 wherein the organosilane treated pigment is made using a silane of the formula:

18. A method as in claim 12 wherein the composition contains a solvent and further comprising the step of removing the solvent from the composition after application to the substrate.

19. A method as in claim 18 wherein the solvent is water.

20. A method as in claim 12 wherein the hydrazide is adipic acid dihydrazide.

21. A method as in claim 12 wherein the polymer is a latex polymer.

22. A method as in claim 12 wherein the organosilane treated pigment is obtained using an epoxy silane in the presence of a diamino silane.

23. A method of preparing a coating composition comprising

combining a polymer having at least one reactive group, a hydrazide group, and

an organosilane treated pigment, the organosilane treated pigment being obtained in-situ during formation of the coating composition, the coating composition containing substantially no isocyanate or formaldehyde.

24. A method as in claim 23 wherein the polymer is a latex polymer.

25. A method as in claim 23 wherein the polymer is an acrylic polymer, modified acrylic polymer, polyepoxide, polyester, polyurethane, polyamide, polyimide, polysiloxane, polycarbonate or a mixture thereof.

26. A method as in claim 23 wherein the at least one reactive group is a carboxyl, hydroxyl, epoxy, amino, keto, silane, silanol, or amido group.

27. A method as in claim 23 wherein the organosilane treated pigment is made using a silane of the formula:

wherein n=1 to 1000;

R is an optionally substituted hydrocarbon group containing from 1 to 20 carbon atoms;

R₁ is the same or different at each occurrence and is a moiety selected from the group consisting of halogen, hydrogen, alkoxy, hydroxy, amino and epoxy groups; and

R₂ can be the same or different at each occurrence and is R or R₁ as defined above.

28. A method as in claim 27 wherein the R₁ in the formula of the silane is an amino or epoxy group.

29. A method as in claim 23 wherein the organosilane treated pigment is made using a silane of the formula:

30. A method as in claim 23 wherein the organosilane treated pigment is obtained using an epoxy silane in the presence of a diamino silane.

31. A method as in claim 23 wherein the method is conducted in the presence of a solvent and the solvent is water.

32. A method as in claim 23 wherein the hydrazide is a polyhydrazide compound.

33. A method as in claim 23 wherein the hydrazide is adipic acid dihydrazide.

34. A coating comprising a polymer crosslinked by an organo group of an organosilane treated pigment, and a hydrazide, the polymer having at least one reactive group, the coating containing substantially no isocyanate or formaldehyde.

35. A coating as in claim 34 wherein the polymer is an acrylic polymer, modified acrylic polymer, polyepoxide, polyester, polyurethane, polyamide, polyimide, polysiloxane, polycarbonate or a mixture thereof.

36. A coating as in claim 34 wherein the at least one reactive group is a carboxyl, hydroxyl, epoxy, amino, keto, silane, silanol, or amido group.

37. A coating as in claim 34 wherein the organosilane treated pigment is made using a silane of the formula:

wherein n=1 to 1000;

R is an optionally substituted hydrocarbon group containing from 1 to 20 carbon atoms;

R₁ is the same or different at each occurrence and is a moiety selected from the group consisting of halogen, hydrogen, alkoxy, hydroxy, amino and epoxy groups; and

R₂ can be the same or different at each occurrence and is R or R₁ as defined above.

38. A coating as in claim 37 wherein the R₁ in the formula of the silane is an amino or epoxy group.

39. A coating as in claim 34 wherein the organosilane treated pigment is made using a silane of the formula:

40. A coating as in claim 34 wherein the hydrazide is adipic acid dihydrazide.

41. A coating as in claim 34 wherein the polymer is a latex polymer.

42. A coating as in claim 34 wherein the organosilane treated pigment is obtained using an epoxy silane in the presence of a diamino silane.

43. A coated substrate comprising a substrate coated with a coating comprising a polymer crosslinked by an organo group of an organosilane treated pigment, and a hydrazide, the polymer having at least one reactive group, the coating containing substantially no isocyanate or formaldehyde.

44. A coated substrate as in claim 43 wherein the polymer is an acrylic polymer, modified acrylic polymer, polyepoxide, polyester, polyurethane, polyamide, polyimide, polysiloxane, polycarbonate or a mixture thereof.

45. A coated substrate as in claim 43 wherein the at least one reactive group is a carboxyl, hydroxyl, epoxy, amino, keto, silane, silanol, or amido group.

46. A coated substrate as in claim 43 wherein the organosilane treated pigment is made using a silane of the formula:

wherein n=1 to 1000;

R is an optionally substituted hydrocarbon group containing from 1 to 20 carbon atoms;

R₁ is the same or different at each occurrence and is a moiety selected from the group consisting of halogen, hydrogen, alkoxy, hydroxy, amino and epoxy groups; and

R₂ can be the same or different at each occurrence and is R or R₁ as defined above.

47. A coated substrate as in claim 46 wherein the R₁ in the formula of the silane is an amino or epoxy group.

48. A coated substrate as in claim 43 wherein the organosilane treated pigment is made using a silane of the formula:

49. A coated substrate as in claim 43 wherein the hydrazide is adipic acid dihydrazide.

57. A coated substrate as in claim 43 wherein the polymer is a latex polymer.

61. A coated substrate as in claim 43 wherein the organosilane treated pigment is obtained using an epoxy silane in the presence of a diamino silane.

50. A coating comprising a polymer crosslinked by an organo group of an organosilane treated pigment, and a hydrazide, the polymer having at least one reactive group and the hydrazide not being attached to the polymer, the coating containing substantially no isocyanate or formaldehyde.

51. A coating as in claim 50 wherein the polymer is an acrylic polymer, modified acrylic polymer, polyepoxide, polyester, polyurethane, polyamide, polyimide, polysiloxane, polycarbonate or a mixture thereof.

52. A coating as in claim 50 wherein the at least one reactive group is a carboxyl, hydroxyl, epoxy, amino, keto, silane, silanol, or amido group.

53. A coating as in claim 50 wherein the organosilane treated pigment is made using a silane of the formula:

wherein n=1 to 1000;

R is an optionally substituted hydrocarbon group containing from 1 to 20 carbon atoms;

R₁ is the same or different at each occurrence and is a moiety selected from the group consisting of halogen, hydrogen, alkoxy, hydroxy, amino and epoxy groups; and

R₂ can be the same or different at each occurrence and is R or R₁ as defined above.

54. A coating as in claim 53 wherein the R₁ in the formula of the silane is an amino or epoxy group.

55. A coating as in claim 50 wherein the organosilane treated pigment is made using a silane of the formula:

56. A coating as in claim 50 wherein the hydrazide is adipic acid dihydrazide.

58. A coating as in claim 50 wherein the polymer is a latex polymer.

62. A coating as in claim 50 wherein the organosilane treated pigment is obtained using an epoxy silane in the presence of a diamino silane.

59. A waterborne coating composition made by combining a polymer having at least one reactive group, a hydrazide having the formula:

silane and pigment;

the silane and pigment reacting in-situ during formation of the coating composition to yield an organosilane treated pigment, the coating composition containing substantially no isocyanate or formaldehyde.

60. A coating composition as in claim 59 wherein the silane is an epoxy silane and the composition further comprises a diamino silane.