IP Library Granted Patent US 12,234,379
Granted Patent B2
US 12,234,379 · App. 17/882,332 · Granted Feb 25, 2025

Multi-stage polymeric latexes, coating compositions containing such latexes, and articles coated therewith

Inventors: Robert M. O'Brien (Monongahela, PA); Mark Stuetelberg (Hiawatha, KS); Joseph D. Desousa (Pittsburgh, PA); Mary Jo Scandolari (Coraopolis, PA); Nikolaus Koch (Greensburg, PA); Stephen Pollin (Ambridge, PA); Nusrah Hussain (Gibsonia, PA)
Assignee: SWIMC LLC
C09D5/027C08F220/06C08F220/14C08F265/06C09D151/003
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,234,379
App. No.
17/882,332
Granted
Feb 25, 2025
Kind
B2
Abstract

An aqueous coating composition is provided that is useful in coating a variety of substrates, including interior or exterior portions of food or beverage cans. The coating composition includes a resin system that includes a multi-stage latex. In some embodiments, the multi-stage latex is formed using a process that includes emulsion polymerizing two or more stages in the presence of an aqueous dispersion including a water-dispersible polymer. In certain preferred embodiments, the water-dispersible polymer is a polyether polymer.

Claims (194)

1. An aqueous coating composition comprising:

a resin system including:

a water-dispersible polymer comprising a solution-polymerized acrylic polymer, a polyether polymer, a polyolefin polymer, a polyester polymer, or a mixture or copolymer thereof; and

a multi-stage polymeric latex having two or more emulsion polymerized stages in an aqueous carrier liquid, wherein the water-dispersible polymer is incorporated into the multi-stage polymeric latex, blended with the multi-stage polymeric latex, or both; the aqueous coating composition is a sprayable composition for a food or beverage container; and wherein the latex has a gradient Tg with at least a 20° C. differential in the calculated Tg of monomers fed at the start of polymerization compared to monomers fed at the end of polymerization; and

wherein the coating composition is substantially free of each of bisphenol A, bisphenol F, and bisphenol S.

2. The coating composition of claim 1 , wherein the two or more emulsion polymerized stages are emulsion polymerized in the presence of the water-dispersible polymer.

3. The coating composition of claim 2 , wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 50:50.

4. The coating composition of claim 3 , wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 40:60.

5. The coating composition of claim 4 , wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 30:70.

6. The coating composition of claim 3 , wherein the water-dispersible polymer has an acid number from 40 to 200 mg KOH per gram.

7. An aqueous coating composition comprising:

a resin system including:

a water-dispersible polymer comprising a solution-polymerized acrylic polymer, a polyether polymer, a polyolefin polymer, a polyester polymer, or a mixture or copolymer thereof; and

a multi-stage polymeric latex having two or more emulsion polymerized stages in an aqueous carrier liquid;

wherein the two or more emulsion polymerized stages are emulsion polymerized in the presence of the water-dispersible polymer;

wherein the water-dispersible polymer is incorporated into the multi-stage polymeric latex, blended with the multi-stage polymeric latex, or both; and

wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 50:50;

wherein the latex has a gradient Tg;

wherein the latex has a lower Tg emulsion polymerized stage having a calculated Tg that is at least 40° C. lower than a calculated Tg of a higher Tg emulsion polymerized stage; and

wherein the aqueous coating composition is a sprayable composition for a food or beverage container; and

wherein the coating composition is substantially free of each of bisphenol A, bisphenol F, and bisphenol S.

8. The coating composition of claim 1 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits:

(i) a global extraction result of less than 50 ppm,

(ii) a metal exposure of less than 3 mA on average when the can is filled with 1% NaCl in deionized water and tested pursuant to the Initial Metal Exposure test method disclosed herein, and

(iii) a metal exposure of less than 10 mA when tested pursuant to the Metal Exposure after Drop Damage test disclosed herein.

9. The coating composition of claim 4 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits:

(i) a global extraction result of less than 50 ppm,

(ii) a metal exposure of less than 3 mA on average when the can is filled with 1% NaCl in deionized water and tested pursuant to the Initial Metal Exposure test method disclosed herein, and

(iii) a metal exposure of less than 3.5 mA when tested pursuant to the Metal Exposure after Drop Damage test disclosed herein.

10. The coating composition of claim 8 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits a lower sidewall adhesion rating value of 9 or 10 after retort in 2% citric acid under pressure at 121° C. and tested according to ASTM D 3359-Test Method B.

11. The coating composition of claim 8 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, is capable of passing a necking and flanging test as indicated by a change of metal exposure after necking of less than 1.0 mA.

12. The coating composition of claim 3 , wherein the resin system does not include and is not derived from any acrylamide-type monomers.

13. The coating composition of claim 1 , wherein the coating composition does not contain formaldehyde or formaldehyde-containing compounds.

14. An aqueous coating composition comprising:

a resin system including:

a water-dispersible polymer having an acid number of at least 40 mg KOH per gram and comprising a solution-polymerized acrylic polymer, a polyether polymer, a polyolefin polymer, a polyester polymer, or a mixture or copolymer thereof;

and a multi-stage polymeric latex having two or more emulsion polymerized stages, wherein the two or more emulsion polymerized stages are emulsion polymerized in the presence of the water-dispersible polymer, and wherein the latex has a gradient Tg with at least a 20° C. differential in the calculated Tg of monomers fed at the start of polymerization compared to monomers fed at the end of polymerization; and

an aqueous carrier liquid that includes at least 5 wt-% of organic solvent; and

wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 50:50; and

wherein the coating composition is an inside spray beverage can coating composition; is substantially free of each of bisphenol A, bisphenol F, and bisphenol S; and has a total solids weight of about 15 to about 25%, based on the total weight of the coating composition.

15. The coating composition of claim 14 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits:

(i) a global extraction result of less than 50 ppm,

(ii) a metal exposure of less than 3 mA on average when the can is filled with 1% NaCl in deionized water and tested pursuant to the Initial Metal Exposure test method disclosed herein,

(iii) a metal exposure of less than 3.5 mA when tested pursuant to the Metal Exposure after Drop Damage test disclosed herein, and

(iv) a lower sidewall adhesion rating value of 9 or 10 after retort in 2% citric acid under pressure at 121° C. and tested according to ASTM D 3359-Test Method B.

16. The coating composition of claim 14 , wherein the resin system does not include and is not derived from any acrylamide-type monomers.

17. The coating composition of claim 14 , wherein the coating composition does not contain formaldehyde or formaldehyde-containing compounds.

18. An aqueous coating composition comprising:

a resin system including:

a water-dispersible polymer comprising a solution-polymerized acrylic polymer, a polyether polymer, a polyolefin polymer, a polyester polymer, or a mixture or copolymer thereof; and

a multi-stage polymeric latex having two or more emulsion polymerized stages in an aqueous carrier liquid, wherein the water-dispersible polymer is incorporated into the multi-stage polymeric latex, blended with the multi-stage polymeric latex, or both; the aqueous coating composition is a sprayable composition for a food or beverage container; and wherein the latex has one or both of:

(i) a lower Tg emulsion polymerized stage having a calculated Tg that is at least 20° C. lower than a calculated Tg of a higher Tg emulsion polymerized stage, or

(ii) a gradient Tg with at least a 20° C. differential in the calculated Tg of monomers fed at the start of polymerization compared to monomers fed at the end of polymerization; and

wherein the coating composition is substantially free of each of bisphenol A, bisphenol F, and bisphenol S; and

wherein the coating composition does not include styrene.

19. The coating composition of claim 18 , wherein the aqueous carrier liquid contains greater than about 5% organic solvent based on the total weight of the aqueous carrier liquid.

20. The coating composition of claim 18 , wherein the two or more emulsion polymerized stages are emulsion polymerized in the presence of the water-dispersible polymer.

21. The coating composition of claim 20 , wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 50:50.

22. The coating composition of claim 21 , wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 40:60.

23. The coating composition of claim 22 , wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 30:70.

24. The coating composition of claim 21 , wherein the water-dispersible polymer has an acid number from 40 to 200 mg KOH per gram.

25. The coating composition of claim 21 , wherein the latex has a lower Tg emulsion polymerized stage having a calculated Tg that is at least 40° C. lower than a calculated Tg of the higher Tg emulsion polymerized stage.

26. The coating composition of claim 18 , wherein more than 50 weight percent of the emulsion polymerized stages have a calculated Tg of at least 40° C.

27. The coating composition of claim 18 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits:

(i) a global extraction result of less than 50 ppm,

(ii) a metal exposure of less than 3 mA on average when the can is filled with 1% NaCl in deionized water and tested pursuant to the Initial Metal Exposure test method disclosed herein, and

(iii) a metal exposure of less than 10 mA when tested pursuant to the Metal Exposure after Drop Damage test disclosed herein.

28. The coating composition of claim 22 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits:

(i) a global extraction result of less than 50 ppm,

(ii) a metal exposure of less than 3 mA on average when the can is filled with 1% NaCl in deionized water and tested pursuant to the Initial Metal Exposure test method disclosed herein, and

(iii) a metal exposure of less than 3.5 mA when tested pursuant to the Metal Exposure after Drop Damage test disclosed herein.

29. The coating composition of claim 27 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits a lower sidewall adhesion rating value of 9 or 10 after retort in 2% citric acid under pressure at 121° C. and tested according to ASTM D 3359-Test Method B.

30. The coating composition of claim 26 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, is capable of passing a necking and flanging test as indicated by a change of metal exposure after necking of less than 1.0 mA.

31. The coating composition of claim 21 , wherein the resin system does not include and is not derived from any acrylamide-type monomers.

32. The coating composition of claim 18 , wherein the coating composition does not contain formaldehyde or formaldehyde-containing compounds.

33. An aqueous coating composition comprising:

a resin system including:

a water-dispersible polymer having an acid number of at least 40 mg KOH per gram and comprising a solution-polymerized acrylic polymer, a polyether polymer, a polyolefin polymer, a polyester polymer, or a mixture or copolymer thereof;

and a multi-stage polymeric latex having two or more emulsion polymerized stages, wherein the two or more emulsion polymerized stages are emulsion polymerized in the presence of the water-dispersible polymer, and wherein the latex has a lower Tg emulsion polymerized stage having a calculated Tg that is at least 30° C. lower than a calculated Tg of a higher Tg emulsion polymerized stage; and

an aqueous carrier liquid that includes at least 5 wt-% of organic solvent; and

wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 50:50; and

wherein the coating composition is an inside spray beverage can coating composition; is substantially free of each of bisphenol A, bisphenol F, and bisphenol S; and has a total solids weight of about 15 to about 25%, based on the total weight of the coating composition; and

wherein the coating composition does not include styrene.

34. The coating composition of claim 33 , wherein more than 50 weight percent of the emulsion polymerized stages have a calculated Tg of at least 50° C.

35. The coating composition of claim 33 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits:

(i) a global extraction result of less than 50 ppm,

(ii) a metal exposure of less than 3 mA on average when the can is filled with 1% NaCl in deionized water and tested pursuant to the Initial Metal Exposure test method disclosed herein,

(iii) a metal exposure of less than 3.5 mA when tested pursuant to the Metal Exposure after Drop Damage test disclosed herein, and

(iv) a lower sidewall adhesion rating value of 9 or 10 after retort in 2% citric acid under pressure at 121° C. and tested according to ASTM D 3359-Test Method B.

36. The coating composition of claim 33 , wherein the resin system does not include and is not derived from any acrylamide-type monomers.

37. The coating composition of claim 33 , wherein the coating composition does not contain formaldehyde or formaldehyde-containing compounds.

38. An aqueous coating composition comprising:

a resin system including:

a water-dispersible polymer comprising a solution-polymerized acrylic polymer, a polyether polymer, a polyolefin polymer, a polyester polymer, or a mixture or copolymer thereof; and

a multi-stage polymeric latex having two or more emulsion polymerized stages in an aqueous carrier liquid, wherein the water-dispersible polymer is incorporated into the multi-stage polymeric latex, blended with the multi-stage polymeric latex, or both; the aqueous coating composition is a sprayable composition for a food or beverage container; and wherein the latex has one or both of:

(i) a lower Tg emulsion polymerized stage having a calculated Tg that is at least 20° C. lower than a calculated Tg of a higher Tg emulsion polymerized stage, or

(ii) a gradient Tg with at least a 20° C. differential in the calculated Tg of monomers fed at the start of polymerization compared to monomers fed at the end of polymerization; and

wherein the coating composition is substantially free of each of bisphenol A, bisphenol F, and bisphenol S; and

wherein the coating composition comprises a beta-hydroxyalkyl-amide crosslinker.

39. The coating composition of claim 38 , wherein the aqueous carrier liquid contains greater than about 5% organic solvent based on the total weight of the aqueous carrier liquid.

40. The coating composition of claim 38 , wherein the two or more emulsion polymerized stages are emulsion polymerized in the presence of the water-dispersible polymer.

41. The coating composition of claim 40 , wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 50:50.

42. The coating composition of claim 41 , wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 40:60.

43. The coating composition of claim 42 , wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 30:70.

44. The coating composition of claim 41 , wherein the water-dispersible polymer has an acid number from 40 to 200 mg KOH per gram.

45. The coating composition of claim 41 , wherein the latex has a lower Tg emulsion polymerized stage having a calculated Tg that is at least 40° C. lower than a calculated Tg of the higher Tg emulsion polymerized stage.

46. The coating composition of claim 38 , wherein more than 50 weight percent of the emulsion polymerized stages have a calculated Tg of at least 40° C.

47. The coating composition of claim 38 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits:

(i) a global extraction result of less than 50 ppm,

(ii) a metal exposure of less than 3 mA on average when the can is filled with 1% NaCl in deionized water and tested pursuant to the Initial Metal Exposure test method disclosed herein, and

(iii) a metal exposure of less than 10 mA when tested pursuant to the Metal Exposure after Drop Damage test disclosed herein.

48. The coating composition of claim 42 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits:

(i) a global extraction result of less than 50 ppm,

(ii) a metal exposure of less than 3 mA on average when the can is filled with 1% NaCl in deionized water and tested pursuant to the Initial Metal Exposure test method disclosed herein, and

(iii) a metal exposure of less than 3.5 mA when tested pursuant to the Metal Exposure after Drop Damage test disclosed herein.

49. The coating composition of claim 47 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits a lower sidewall adhesion rating value of 9 or 10 after retort in 2% citric acid under pressure at 121° C. and tested according to ASTM D 3359-Test Method B.

50. The coating composition of claim 46 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, is capable of passing a necking and flanging test as indicated by a change of metal exposure after necking of less than 1.0 mA.

51. The coating composition of claim 41 , wherein the resin system does not include and is not derived from any acrylamide-type monomers.

52. The coating composition of claim 38 , wherein the coating composition does not contain formaldehyde or formaldehyde-containing compounds.

53. An aqueous coating composition comprising:

a resin system including:

a water-dispersible polymer having an acid number of at least 40 mg KOH per gram and comprising a solution-polymerized acrylic polymer, a polyether polymer, a polyolefin polymer, a polyester polymer, or a mixture or copolymer thereof;

and a multi-stage polymeric latex having two or more emulsion polymerized stages, wherein the two or more emulsion polymerized stages are emulsion polymerized in the presence of the water-dispersible polymer, and wherein the latex has a lower Tg emulsion polymerized stage having a calculated Tg that is at least 30° C. lower than a calculated Tg of a higher Tg emulsion polymerized stage; and

an aqueous carrier liquid that includes at least 5 wt-% of organic solvent; and

wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 50:50; and

wherein the coating composition is an inside spray beverage can coating composition; is substantially free of each of bisphenol A, bisphenol F, and bisphenol S; and has a total solids weight of about 15 to about 25%, based on the total weight of the coating composition; and

wherein the coating composition comprises a beta-hydroxyalkyl-amide crosslinker.

54. The coating composition of claim 53 , wherein more than 50 weight percent of the emulsion polymerized stages have a calculated Tg of at least 50° C.

55. The coating composition of claim 53 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits:

(i) a global extraction result of less than 50 ppm,

(ii) a metal exposure of less than 3 mA on average when the can is filled with 1% NaCl in deionized water and tested pursuant to the Initial Metal Exposure test method disclosed herein,

(iii) a metal exposure of less than 3.5 mA when tested pursuant to the Metal Exposure after Drop Damage test disclosed herein, and

(iv) a lower sidewall adhesion rating value of 9 or 10 after retort in 2% citric acid under pressure at 121° C. and tested according to ASTM D 3359-Test Method B.

56. The coating composition of claim 53 , wherein the resin system does not include and is not derived from any acrylamide-type monomers.

57. The coating composition of claim 53 , wherein the coating composition does not contain formaldehyde or formaldehyde-containing compounds.

58. An aqueous coating composition comprising:

a resin system including:

a water-dispersible polymer comprising at least one of an aromatic polyether polymer and a polyether-acrylate copolymer; and

a multi-stage polymeric latex having two or more emulsion polymerized stages in an aqueous carrier liquid, wherein the water-dispersible polymer is incorporated into the multi-stage polymeric latex, blended with the multi-stage polymeric latex, or both; the aqueous coating composition is a sprayable composition for a food or beverage container; and wherein the latex has one or both of:

(i) a lower Tg emulsion polymerized stage having a calculated Tg that is at least 20° C. lower than a calculated Tg of a higher Tg emulsion polymerized stage, or

(ii) a gradient Tg with at least a 20° C. differential in the calculated Tg of monomers fed at the start of polymerization compared to monomers fed at the end of polymerization; and

wherein the coating composition is substantially free of each of bisphenol A, bisphenol F, and bisphenol S.

59. The coating composition of claim 58 , wherein the aqueous carrier liquid contains greater than about 5% organic solvent based on the total weight of the aqueous carrier liquid.

60. The coating composition of claim 58 , wherein the two or more emulsion polymerized stages are emulsion polymerized in the presence of the water-dispersible polymer.

61. The coating composition of claim 60 , wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 50:50.

62. The coating composition of claim 61 , wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 40:60.

63. The coating composition of claim 62 , wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 30:70.

64. The coating composition of claim 58 , wherein the water-dispersible polymer comprises a polyether polymer formed from reactants including (i) an extender and (ii) a diepoxide of: an aromatic diol, an aromatic diacid, an aliphatic diol, an aliphatic diacid, a cycloaliphatic diol, a cycloaliphatic diacid, or a combination thereof.

65. The coating composition of claim 61 , wherein the water-dispersible polymer has an acid number from 40 to 200 mg KOH per gram.

66. The coating composition of claim 61 , wherein the latex has a lower Tg emulsion polymerized stage having a calculated Tg that is at least 40° C. lower than a calculated Tg of the higher Tg emulsion polymerized stage.

67. The coating composition of claim 58 , wherein more than 50 weight percent of the emulsion polymerized stages have a calculated Tg of at least 40° C.

68. The coating composition of claim 58 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits:

(i) a global extraction result of less than 50 ppm,

(ii) a metal exposure of less than 3 mA on average when the can is filled with 1% NaCl in deionized water and tested pursuant to the Initial Metal Exposure test method disclosed herein, and

(iii) a metal exposure of less than 10 mA when tested pursuant to the Metal Exposure after Drop Damage test disclosed herein.

69. The coating composition of claim 62 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits:

(i) a global extraction result of less than 50 ppm,

(ii) a metal exposure of less than 3 mA on average when the can is filled with 1% NaCl in deionized water and tested pursuant to the Initial Metal Exposure test method disclosed herein, and

(iii) a metal exposure of less than 3.5 mA when tested pursuant to the Metal Exposure after Drop Damage test disclosed herein.

70. The coating composition of claim 68 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits a lower sidewall adhesion rating value of 9 or 10 after retort in 2% citric acid under pressure at 121° C. and tested according to ASTM D 3359-Test Method B.

71. The coating composition of claim 67 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, is capable of passing a necking and flanging test as indicated by a change of metal exposure after necking of less than 1.0 mA.

72. The coating composition of claim 61 , wherein the resin system does not include and is not derived from any acrylamide-type monomers.

73. The coating composition of claim 58 , wherein the coating composition does not contain formaldehyde or formaldehyde-containing compounds.

74. An aqueous coating composition comprising:

a resin system including:

a water-dispersible polymer having an acid number of at least 40 mg KOH per gram and comprising at least one of an aromatic polyether polymer and a polyether-acrylate copolymer;

and a multi-stage polymeric latex having two or more emulsion polymerized stages, wherein the two or more emulsion polymerized stages are emulsion polymerized in the presence of the water-dispersible polymer, and wherein the latex has a lower Tg emulsion polymerized stage having a calculated Tg that is at least 30° C. lower than a calculated Tg of a higher Tg emulsion polymerized stage; and

an aqueous carrier liquid that includes at least 5 wt-% of organic solvent; and

wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 50:50; and

wherein the coating composition is an inside spray beverage can coating composition; is substantially free of each of bisphenol A, bisphenol F, and bisphenol S; and has a total solids weight of about 15 to about 25%, based on the total weight of the coating composition.

75. The coating composition of claim 74 , wherein more than 50 weight percent of the emulsion polymerized stages have a calculated Tg of at least 50° C.

76. The coating composition of claim 74 , wherein the coating composition, when spray applied onto an interior of a 355 mL no. 211 two-piece drawn and ironed aluminum beverage can at 115 milligrams per can coating weight and cured at 188° C. to 199° C. (measured at the can dome) for 55 seconds, exhibits:

(i) a global extraction result of less than 50 ppm,

(ii) a metal exposure of less than 3 mA on average when the can is filled with 1% NaCl in deionized water and tested pursuant to the Initial Metal Exposure test method disclosed herein,

(iii) a metal exposure of less than 3.5 mA when tested pursuant to the Metal Exposure after Drop Damage test disclosed herein, and

(iv) a lower sidewall adhesion rating value of 9 or 10 after retort in 2% citric acid under pressure at 121° C. and tested according to ASTM D 3359-Test Method B.

77. The coating composition of claim 74 , wherein the resin system does not include and is not derived from any acrylamide-type monomers.

78. The coating composition of claim 74 , wherein the coating composition does not contain formaldehyde or formaldehyde-containing compounds.

79. An aqueous coating composition comprising:

a resin system including:

a water-dispersible polymer comprising a solution-polymerized acrylic polymer, a polyether polymer, a polyolefin polymer, a polyester polymer, or a mixture or copolymer thereof; and

a multi-stage polymeric latex having two or more emulsion polymerized stages in an aqueous carrier liquid, wherein the water-dispersible polymer is incorporated into the multi-stage polymeric latex, blended with the multi-stage polymeric latex, or both; the aqueous coating composition is a sprayable composition for a food or beverage container; and wherein the latex has one or both of:

(i) a lower Tg emulsion polymerized stage having a calculated Tg that is at least 20° C. lower than a calculated Tg of a higher Tg emulsion polymerized stage, or

(ii) a gradient Tg with at least a 20° C. differential in the calculated Tg of monomers fed at the start of polymerization compared to monomers fed at the end of polymerization; and

wherein the coating composition is substantially free of each of bisphenol A, bisphenol F, and bisphenol S; and

wherein polymerization of the lower Tg emulsion polymerized stage is initiated before initiating polymerization of the higher Tg emulsion polymerized stage.

80. An aqueous coating composition comprising:

a resin system including:

a water-dispersible polymer having an acid number of at least 40 mg KOH per gram and comprising a solution-polymerized acrylic polymer, a polyether polymer, a polyolefin polymer, a polyester polymer, or a mixture or copolymer thereof;

and a multi-stage polymeric latex having two or more emulsion polymerized stages, wherein the two or more emulsion polymerized stages are emulsion polymerized in the presence of the water-dispersible polymer, and wherein the latex has a lower Tg emulsion polymerized stage having a calculated Tg that is at least 30° C. lower than a calculated Tg of a higher Tg emulsion polymerized stage; and

an aqueous carrier liquid that includes at least 5 wt-% of organic solvent; and

wherein the weight ratio of water-dispersible polymer to emulsion polymerized stages is less than 50:50; and

wherein the coating composition is an inside spray beverage can coating composition; is substantially free of each of bisphenol A, bisphenol F, and bisphenol S; and has a total solids weight of about 15 to about 25%, based on the total weight of the coating composition; and

wherein polymerization of the lower Tg emulsion polymerized stage is initiated before initiating polymerization of the higher Tg emulsion polymerized stage.

Continuity (5)
Continuation 16805602 · Feb 28, 2020
Continuation PCTUS2018049143 · Aug 31, 2018
Provisional Application 62725204 · Aug 30, 2018
Provisional Application 62553309 · Sep 1, 2017
Related Publication 20230047189A1 · Feb 16, 2023
References Cited (140)
US 3943187A · Wu · 1976 [cited by applicant]
US 4071163A · Martin · 1978 [cited by applicant]
US 4071463A · Steinhauer · 1978 [cited by applicant]
US 4076676A · Sommerfeld · 1978 [cited by applicant]
US 4150005A · Gehman et al. · 1979 [cited by applicant]
US 4247439A · Matthews et al. · 1981 [cited by applicant]
US 4285847A · Ting · 1981 [cited by applicant]
US 4289674A · Christenson et al. · 1981 [cited by applicant]
US 4305859A · McEwan et al. · 1981 [cited by applicant]
US 4413015A · Anderson et al. · 1983 [cited by applicant]
US 4443568A · Woo · 1984 [cited by applicant]
US 4446258A · Chu et al. · 1984 [cited by applicant]
US 4476262A · Chu et al. · 1984 [cited by applicant]
US 4487859A · Martino · 1984 [cited by applicant]
US 4499212A · Martino · 1985 [cited by applicant]
US 4503173A · Martino et al. · 1985 [cited by applicant]
US 4522961A · Martino et al. · 1985 [cited by applicant]
US 4522962A · Abbey et al. · 1985 [cited by applicant]
US 4684708A · Deets et al. · 1987 [cited by applicant]
US 4948834A · Baker et al. · 1990 [cited by applicant]
US 4963602A · Patel · 1990 [cited by applicant]
US 5043380A · Cole · 1991 [cited by applicant]
US 5157078A · Woo et al. · 1992 [cited by applicant]
US 5201436A · Owens et al. · 1993 [cited by applicant]
US 5264469A · Mysliwczyk et al. · 1993 [cited by applicant]
US 5296525A · Spencer · 1994 [cited by applicant]
US 5306763A · Matsumoto et al. · 1994 [cited by applicant]
US 5308890A · Snyder · 1994 [cited by applicant]
US 5387625A · Parekh et al. · 1995 [cited by applicant]
US 5527840A · Chutko et al. · 1996 [cited by applicant]
US 5532297A · Woo et al. · 1996 [cited by applicant]
US 5714539A · Perez et al. · 1998 [cited by applicant]
US 5830952A · Pedersen et al. · 1998 [cited by applicant]
US 5869552A · Pedersen et al. · 1999 [cited by applicant]
US 5877239A · Craun et al. · 1999 [cited by applicant]
US 5922817A · Pedersen et al. · 1999 [cited by applicant]
US 6008273A · Leibelt et al. · 1999 [cited by applicant]
US 6710113B2 · Weitzel · 2004 [cited by applicant]
US 6992121B1 · Peters et al. · 2006 [cited by applicant]
US 7037584B2 · Wind et al. · 2006 [cited by applicant]
US 7189787B2 · O'Brien et al. · 2007 [cited by applicant]
US 7592047B2 · O'Brien et al. · 2009 [cited by applicant]
US 7682699B2 · Wind et al. · 2010 [cited by applicant]
US 7695770B2 · Dombrowski · 2010 [cited by applicant]
US 8057893B2 · Killilea et al. · 2011 [cited by applicant]
US 8092876B2 · O'Brien et al. · 2012 [cited by applicant]
US 8105744B2 · Matsumura · 2012 [cited by applicant]
US 8142868B2 · O'Brien et al. · 2012 [cited by applicant]
US 8173265B2 · O'Brien et al. · 2012 [cited by applicant]
US 8202578B2 · Killilea et al. · 2012 [cited by applicant]
US 8617663B2 · O'Brien et al. · 2013 [cited by applicant]
US 8835012B2 · O'Brien et al. · 2014 [cited by applicant]
US 8907005B2 · Dombrowski et al. · 2014 [cited by applicant]
US 8932718B2 · Garner et al. · 2015 [cited by applicant]
US 9012027B2 · Nabuurs et al. · 2015 [cited by applicant]
US 9029470B2 · Rademacher et al. · 2015 [cited by applicant]
US 9181448B2 · Li et al. · 2015 [cited by applicant]
US 9242763B2 · O'Brien et al. · 2016 [cited by applicant]
US 9394456B2 · Rademacher et al. · 2016 [cited by applicant]
US 9404006B2 · Li · 2016 [cited by applicant]
US 9409219B2 · Niederst et al. · 2016 [cited by applicant]
US 9415900B2 · O'Brien et al. · 2016 [cited by applicant]
US 9862854B2 · O'Brien et al. · 2018 [cited by applicant]
US 10023997B2 · Haven et al. · 2018 [cited by applicant]
US 20030059618A1 · Takai · 2003 [cited by applicant]
US 20040236005A1 · Scheerder et al. · 2004 [cited by applicant]
US 20060100366A1 · O'Brien · 2006 [cited by examiner]
US 20070265391A1 · Yang et al. · 2007 [cited by applicant]
US 20080075868A1 · Dombrowski et al. · 2008 [cited by applicant]
US 20090012207A1 · Leyrer et al. · 2009 [cited by applicant]
US 20100068433A1 · Gibanel et al. · 2010 [cited by applicant]
US 20120302690A1 · Cunningham et al. · 2012 [cited by applicant]
US 20130105472A1 · Beaudry et al. · 2013 [cited by applicant]
US 20130281574A1 · Li et al. · 2013 [cited by applicant]
US 20130316109A1 · Niederst et al. · 2013 [cited by applicant]
US 20150004420A1 · Hill et al. · 2015 [cited by applicant]
US 20150031830A1 · Wu · 2015 [cited by applicant]
US 20150197597A1 · Gallucci et al. · 2015 [cited by applicant]
US 20150197657A1 · Niederst et al. · 2015 [cited by applicant]
US 20160009941A1 · Rademacher · 2016 [cited by applicant]
US 20160024325A1 · Li · 2016 [cited by applicant]
US 20160145430A1 · Junk et al. · 2016 [cited by applicant]
US 20160297994A1 · Kuo et al. · 2016 [cited by applicant]
US 20160376446A1 · Gibanel et al. · 2016 [cited by applicant]
US 20170002227A1 · Gibanel et al. · 2017 [cited by applicant]
US 20170096521A1 · Niederst et al. · 2017 [cited by applicant]
US 20170369603A1 · Gibanel et al. · 2017 [cited by applicant]
US 20180305492A1 · Taden et al. · 2018 [cited by applicant]
CN 105315735A · 2016 [cited by applicant]
EP 0256391 · 1988 [cited by applicant]
EP 256391A · 1988 [cited by examiner]
EP 0101307B1 · 1989 [cited by applicant]
EP 0401565A1 · 1990 [cited by applicant]
EP 0590984A1 · 1994 [cited by applicant]
GB 1555868 · 1979 [cited by applicant]
GB 1574721 · 1980 [cited by applicant]
JP 5339387 · 1978 [cited by applicant]
JP 5043830 · 1998 [cited by applicant]
JP 2002155234 · 2002 [cited by applicant]
JP 2008001888 · 2008 [cited by applicant]
JP 2016065130 · 2016 [cited by applicant]
KR 20100137850 · 2010 [cited by applicant]
WO WO199514063 · 1995 [cited by applicant]
WO WO02064691A2 · 2002 [cited by applicant]
WO WO03029300A1 · 2003 [cited by examiner]
WO WO2005121595 · 2005 [cited by applicant]
WO WO2010097353 · 2010 [cited by applicant]
WO WO2011009024 · 2011 [cited by applicant]
WO WO2012089747 · 2012 [cited by applicant]
WO WO2012170623 · 2012 [cited by applicant]
WO WO2013191825 · 2013 [cited by applicant]
WO WO2014025411 · 2014 [cited by applicant]
WO WO2014134442 · 2014 [cited by applicant]
WO WO2014139971 · 2014 [cited by applicant]
WO WO2014139973 · 2014 [cited by applicant]
WO WO2015002958 · 2015 [cited by applicant]
WO WO2015002961 · 2015 [cited by applicant]
WO WO2015015827 · 2015 [cited by applicant]
WO WO2015121595 · 2015 [cited by applicant]
WO WO2015158588A1 · 2015 [cited by applicant]
WO WO2016105502A1 · 2016 [cited by applicant]
WO WO2016105504A1 · 2016 [cited by applicant]
WO WO2016196174A1 · 2016 [cited by applicant]
WO WO2016196190A1 · 2016 [cited by applicant]
WO WO2017079437A1 · 2017 [cited by applicant]
WO WO20170012837 · 2017 [cited by applicant]
WO WO2017180895A1 · 2017 [cited by applicant]
WO WO2018013766A1 · 2018 [cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2018/049059 date mailed Nov. 19, 2018. [cited by applicant]
International Search Report and Written Opinion for International Application No. PCT/US2018/049143 date mailed Dec. 21, 2018. [cited by applicant]
Wikipedia, “Acid Dissociation Constant”, Feb. 17, 2019. https://en.wikipedia.org/wiki/Acid_dissociation_constant. [cited by applicant]
Wikipedia, “Vinyl group”, Nov. 20, 2018. https://en.wikipedia.org/Vinyl_group. [cited by applicant]
Teng et al., “Effect of Introduction Mode of Hydroxyl Functionality on Morphology and Film Properties of Cycloaliphatic Diepoxide Crosslinkable Core-Shell Latex”, Journal of Polymer Science Part A Polymer Chemistry 40(2… [cited by applicant]
Chakraborty et al., “Assessment of Solubilization Characteristics of Different Surfactants for Carvedilol Phosphate as a Function of pH”, Journal of Colloid and Interface Science 335 (2009) 242-249. [cited by applicant]
Cytec, “Specialty Additives: Surfactants for Emulsion Polymerization and Specialty Applications,” 2010, 7 pages. [cited by applicant]
Adeka Corporation, “New Reactive Surfactant ADEKA REASOAP ER/SR Series Technical Datasheet,” Sep. 30, 2011, 8 pages. [cited by applicant]
The Polymer Property Database accessed online at https:polymerdatabase.com/polymer%20Physics/Polymer%20Tg.html, 6 pages, 2021. [cited by applicant]
Sigma-Aldrich, Dihexyl sodium sulfosuccinate for synthesis, Jul. 2020, 2 pages. [cited by applicant]
GEO Specialty Chemicals, “Bisomer PEM 6 LD Technical Data Sheet,” Oct. 2020, 2 pages. [cited by applicant]
Notice of Rejection from JP Patent Appln No. 2020-511960 dated Apr. 12, 2022, 13 pages. [cited by applicant]