Compositions for containers and other articles and methods of using same

• US 9,409,219 B2
• Filed: 08/09/2012
• Issued: 08/09/2016
• Est. Priority Date: 02/07/2011
• Status: Active Grant

• Current Assignee: Swimc, LLC (The Sherwin-Williams Company)
• Original Assignee: Valspar Sourcing, Inc. (Sherwin-Williams Company)
• Inventors: Niederst, Jeffrey, Evans, Richard H., O'Brien, Robert M., Romagnoli, Kevin, Von Maier, Mark S.
• Primary Examiner(s): Blackwell, Gwendolyn
• Assistant Examiner(s): Strah, Eli D
• Application Number:
  US13/570,632
• Publication Number:
  US 20130206756A1
• Time in Patent Office: 1,461 Days
• Field of Search: 428/35.7, 428/35.8, 428/35.9, 220/62.11, 220/62.12, 220/62.13, 523/400
• US Class Current: 1/1
• CPC Class Codes: B05D 2202/00 Metallic substrate
• CPC Class Codes: B05D 7/227 of containers, cans or the like
• CPC Class Codes: B21D 5/00 Bending sheet metal along straight lines, e.g. to form simple curves B21D11/06 - B21D11/18 take precedence; corrugating sheet metal B21D13/00; as edge treatment B21D19/00
• CPC Class Codes: B65D 25/14 Linings or internal coatings of containers made by folding or erecting blanks made of paper B65D5/56 ; linings for domestic water storage heaters F24H1/183
• CPC Class Codes: C08G 59/00 Polycondensates containing more than one epoxy group per molecule low-molecular-weight polyepoxy compounds C07; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
• CPC Class Codes: C08G 65/00 Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
• CPC Class Codes: C09D 163/00 Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• CPC Class Codes: C09D 5/03 Powdery paints
• CPC Class Codes: C09D 5/031 characterised by particle size or shape
• CPC Class Codes: C09D 5/033 characterised by the additives
• CPC Class Codes: C09D 5/037 Rheology improving agents, e.g. flow control agents
• CPC Class Codes: C09D 5/08 Anti-corrosive paints
• CPC Class Codes: Y10T 428/1355 Elemental metal containing [e.g., substrate, foil, film, coating, etc.]

Abstract

This invention provides a polymer, which is preferably a polyether polymer. The polymer may be used in coating compositions. Containers and other articles comprising the polymer and methods of making such containers and other articles are also provided. The invention further provides compositions including the polymer (e.g., powder coatings), which have utility in a variety of coating end uses, including, for example, valve and pipe coatings.

Claims

1. An article comprising:

a food or beverage container, or a portion thereof, having a metal substrate and a coating composition applied on at least a portion of the metal substrate, wherein the coating composition comprises a polyether polymer that;

(a) includes at least 25% by weight of aryl or heteroaryl groups and (b) is substantially free of bound bisphenol A, bisphenol F, bisphenol S, polyhydric phenols having estrogenic activity greater than or equal to that of bisphenol S, and epoxides thereof; and

wherein the polymer is formed by reacting ingredients including;

(i) an extender comprising a dihydric phenol that does not include substituent groups at ortho ring positions relative to the phenol hydroxyl groups and (ii) a diepoxide compound that includes a segment of the below Formula (I);

2. The article of claim 1, wherein the polyether polymer includes at least 25% by weight of phenylene groups and each of the depicted oxygen atoms are present in an ether linkage.

3. The article of claim 1, wherein the polyether polymer includes at least 45% by weight of phenylene groups.

4. The article of claim 1, wherein each R¹ is free of halogen atoms.

5. The article of claim 4, wherein each R¹ is independently a methyl group, an ethyl group, a propyl group, a butyl group, or an isomer thereof.

6. The article of claim 1, wherein each depicted oxygen atom in Formula (I) is located at a para position relative to R².

7. The article of claim 1, wherein the segment of Formula (I) has an atomic weight of less than 600 Daltons.

8. The article of claim 1, wherein the segments of Formula (I) constitute at least 30% by weight of the polyether polymer.

9. The article of claim 1, wherein the diepoxide compound is non-genotoxic and is derived from a dihydric phenol that that exhibits a log Relative Proliferative Effect value in the MCF-7 cell proliferation assay of less than −

3.

10. The article of claim 1, wherein the diepoxide compound comprises the diglycidyl ether of 4,4′

-methylenebis(2,6-dimethylphenol).

11. The article of claim 1, wherein the dihydric phenol comprises catechol, hydroquinone, or resorcinol.

12. The article of claim 1, wherein the depicted oxygen atoms are each present in an ether linkage and the polymer includes —

CH₂—

CH(OH)—

CH₂—

or —

CH₂—

CH₂—

CH(OH)—

segments.

13. The article of claim 1, wherein the polymer has a glass transition temperature of at least 60°

C.

14. The article of claim 1, wherein the food or beverage container, or a portion thereof, has the coating composition applied as a food-contact coating on an interior surface.

15. The article of claim 1, wherein the polyether polymer is completely free of bound polyhydric phenols, or epoxides thereof, having estrogenic activity greater than that of 4,4′

-(propane-2,2-diyl)bis(2,6-dibromophenol).

16. The article of claim 1, wherein the polyether polymer is completely free of bound polyhydric phenols, or epoxides thereof, having estrogenic activity greater than that of 2,2-bis(4-hydroxyphenyl)propanoic acid.

17. The article of claim 1, wherein the polymer has a glass transition temperature of at least 80°

C.

18. The article of claim 1, wherein both depicted phenylene groups include a methyl moiety at an ortho ring position relative to each depicted oxygen atom.

19. The article of claim 1, wherein v is independently 2 to 4.

20. The article of claim 1, wherein the coating composition is a thermoset coating composition.

21. A coating composition, comprising:

a polyether polymer that includes at least 25% by weight of aryl or heteroaryl groups, has a glass transition temperature of at least 30°

C. and a number average molecular weight of at least 2,000, and is substantially free of bound bisphenol A, bisphenol F, bisphenol S, polyhydric phenols having estrogenic activity greater than or equal to that of bisphenol S, and epoxides thereof; and

wherein the polymer is formed by reacting ingredients including;

(i) an extender comprising a dihydric phenol that does not include substituent groups at ortho ring positions relative to the phenol hydroxyl groups and (ii) a diepoxide compound that includes a segment of the below Formula (I);

22. The coating composition of claim 21, wherein the polyether polymer has a glass transition temperature of at least 80°

C.

23. The coating composition of claim 21, wherein the polyether polymer is completely free of bound polyhydric phenols, or epoxides thereof, having estrogenic activity greater than that of 4,4′

-(propane-2,2-diyl)bis(2,6-dibromophenol).

24. The coating composition of claim 21, wherein the polyether polymer is completely free of bound polyhydric phenols, or epoxides thereof, having estrogenic activity greater than that of 2,2-bis(4-hydroxyphenyl)propanoic acid.

25. The coating composition of claim 21, wherein:

the coating composition includes a liquid carrier;

the polyether polymer has a glass transition temperature of at least 60°

C.; and

the segment of Formula (I) has an atomic weight of less than 1,000 Daltons and is free of halogen atoms.

26. The coating composition of claim 25, wherein the polyether polymer has a polydispersity index of from 1.5 to 5, and wherein the segments of Formula (I) constitute at least 30% by weight of the polyether polymer.

27. The coating composition of claim 26, wherein the diepoxide compound is non-genotoxic.

28. The coating composition of claim 25, wherein the polyether polymer has a polydispersity index of from 2 to 3.5, and wherein the diepoxide compound is non-genotoxic.

29. The coating composition of claim 25, wherein:

the coating composition comprises, by weight total resin solids, at least 30% by weight of the polyether polymer; and

the extender comprises a polyol, and wherein the polyol comprises a dihydric phenol.

30. The coating composition of claim 25, wherein the polyether polymer has a number average molecular weight of at least 4,000.

31. The coating composition of claim 21, wherein the diepoxide compound comprises the diglycidyl ether of 4,4′

-methylenebis(2,6-dimethylphenol).

32. The coating composition of claim 21, wherein the segment of Formula (I) is free of halogen atoms.

33. The coating composition of claim 21, wherein the segment of Formula (I) is free of halogen atoms and the segment of Formula (I) has an atomic weight of less than 600 Daltons.

34. The coating composition of claim 21, wherein the polyether polymer has a Tg of from at least 80°

C. to less than 110°

C.

35. The coating composition of claim 21, wherein the coating composition is an organic solvent-based coating composition that includes from at least 20% to no greater than 40% by weight non-volatile components.

36. The coating composition of claim 21, wherein the coating composition is a water-based coating composition having no greater than 50% by weight non-volatile components.

37. The coating composition of claim 21, wherein both depicted phenylene groups includes an R¹ group located at an ortho ring position, relative to each depicted oxygen atom, that is a methyl moiety.

38. The coating composition of claim 21, wherein v is independently 2 to 4.

39. The coating composition of claim 21, wherein the coating composition is a thermoset coating composition that includes a liquid carrier.

40. An article comprising:

a food or beverage container, or a portion thereof, having a metal substrate and a food-contact coating applied on at least a portion of an interior surface of the metal substrate, wherein the food-contact coating is formed from a liquid coating composition that comprises, by weight total resin solids, at least 10% by weight of a polyether polymer that;

(a) has a number average molecular weight of at least 2,000, (b) includes at least 25% by weight of phenylene groups, (c) has a Tg of at least 60°

C., and (d) is substantially free of bound bisphenol A, bisphenol F, bisphenol S, polyhydric phenols having estrogenic activity greater than or equal to that of bisphenol S, and epoxides thereof; and

wherein the polymer is formed by reacting ingredients including;

(i) an extender comprising a dihydric phenol that does not include substituent groups at ortho ring positions relative to the phenol hydroxyl groups and (ii) a diepoxide compound that includes a segment of the below Formula (I);

41. The article of claim 40, wherein the segment of Formula (I) is free of halogen atoms.

42. The article of claim 41, wherein each R¹ is independently a carbon-containing group having an atomic weight of at least 15 Daltons to less than 500 Daltons.

43. The article of claim 41, wherein the diepoxide compound is non-genotoxic.

44. The article of claim 42, wherein each R¹ is independently a methyl moiety, an ethyl moiety, a propyl moiety, a butyl moiety, or an isomer thereof.

45. The article of claim 43, wherein the polyether polymer has a polydispersity index of from 1.5 to 5.

46. The article of claim 40, wherein the polyether polymer has a polydispersity index of from 2 to 3.5.

47. The article of claim 40, wherein:

the segment of Formula (I) has an atomic weight of less than 1,000 Daltons;

the polyether polymer is free of halogen atoms and has a number average molecular weight of at least 3,000;

the polyether polymer includes at least 45% by weight of phenylene groups; and

the coating composition comprises, by weight total resin solids, at least 30% by weight of the polyether polymer.

48. The article of claim 47, wherein the polyether polymer is completely free of bound polyhydric phenols, or epoxides thereof, having estrogenic activity greater than that of 2,2-bis(4-hydroxyphenyl)propanoic acid.

49. The article of claim 43, wherein the coating composition comprises, by weight total resin solids, at least 30% by weight of the polyether polymer.

50. The article of claim 41, wherein the coating composition comprises, by weight total resin solids, at least 50% by weight of the polyether polymer.

51. The article of claim 41, wherein the segment of Formula (I) has an atomic weight of less than 1,000 Daltons.

52. The article of claim 41, wherein the segment of Formula (I) has an atomic weight of less than 600 Daltons.

53. The article of claim 43, wherein the polyether polymer includes at least 45% by weight of phenylene groups.

54. The article of claim 43, wherein the polyether polymer is completely free of bound polyhydric phenols, or epoxides thereof, having estrogenic activity greater than that of 4,4′

-(propane-2,2-diyl)bis(2,6-dibromophenol).

55. The article of claim 40, wherein the polyether polymer is free of halogen atoms and is completely free of bound polyhydric phenols, or epoxides thereof, having estrogenic activity greater than that of 2,2-bis(4-hydroxyphenyl)propanoic acid.

56. The article of claim 43, wherein the dihydric phenol comprises catechol, hydroquinone, or resorcinol.

57. The article of claim 43, wherein the polyether polymer has a polydispersity index of from 2 to 3.5.

58. The article of claim 41, wherein the polyether polymer has a Tg of at least 70°

C.

59. The article of claim 43, wherein the polyether polymer has a Tg of at least 80°

C.

60. The article of claim 40, wherein the polyether polymer has a Tg of at least 60°

C. and less than 150°

C.

61. The article of claim 43, wherein the polyether polymer has a Tg of at least 60°

C. and less than 130°

C.

62. The article of claim 41, wherein the polyether polymer has a Tg of from at least 80°

C. to less than 110°

C.

63. The article of claim 40, wherein the diepoxide compound comprises the diglycidyl ether of 4,4′

-methylenebis(2,6-dimethylphenol).

64. The article of claim 40, wherein the food or beverage container or a portion thereof comprises a two-piece aluminum beer or beverage can.

65. The article of claim 43, wherein the food or beverage container or a portion thereof comprises a two-piece aluminum beer or beverage can, and wherein the coating is an inside spray coating.

66. The article of claim 65, wherein the inside spray coating exhibits a metal exposure value of less than 3.5 mA after the two-piece aluminum beer or beverage can is filled with water and dropped twice from a height of 24 inches through a cylindrical tube having a 2 and ⅞

inch internal diameter, can bottom down, onto an impact wedge;

wherein the orientation of the can in the second drop is rotated 180 degrees relative to the orientation of the can in the first drop; and

wherein a 1% NaCl in deionized water electrolyte solution is used to determine the metal exposure value.

67. The article of claim 40, wherein both depicted phenylene groups include a methyl moiety at an ortho ring position relative to each depicted oxygen atom.

68. The article of claim 40, wherein v is independently 2 to 4.

69. The article of claim 40, wherein the liquid coating composition is a thermoset coating composition.