Compositions for containers and other articles and methods of using same

• US 10,294,388 B2
• Filed: 07/07/2016
• Issued: 05/21/2019
• Est. Priority Date: 02/07/2011
• Status: Active Grant

• Current Assignee: Swimc, LLC (Sherwin-Williams Company)
• Original Assignee: Swimc, LLC (Sherwin-Williams Company)
• Inventors: Niederst, Jeffrey, Evans, Richard H., O'Brien, Robert M., Romagnoli, Kevin, Von Maier, Mark S.
• Primary Examiner(s): Wood, Ellen S
• Application Number:
  US15/204,559
• Publication Number:
  US 20170029657A1
• Time in Patent Office: 1,048 Days
• Field of Search: 428 357, 428 358, 428 359, 220 6211, 220 6212, 220 6213, 523400
• 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 uses 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 applied on at least a portion of the metal substrate;

wherein the coating is substantially free of 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 coating is formed from a coating composition that includes a polyether polymer prepared from 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 R² is —

CH₂—

.

3. The article of claim 1, wherein R² includes at least 10 carbon atoms.

4. The article of claim 1, wherein R² includes at least 12 carbon atoms.

5. The article of claim 1, wherein R² includes 8 to 15 carbon atoms.

6. The article of claim 1, wherein R² includes 10 to 15 carbon atoms.

7. The article of claim 1, wherein R² has an atomic weight of less than 500 Daltons.

8. The article of claim 1, wherein R² includes at least 8 carbon atoms and includes one or more cyclic groups.

9. The article of claim 8, wherein the carbon atom of R² that is attached to a carbon atom of each of the depicted phenylene groups is not present in a monocyclic cyclohexyl group.

10. The article of claim 8, wherein the one or more cyclic groups comprises one or more aromatic groups.

11. The article of claim 9, wherein the one or more cyclic groups comprises one or more alicyclic groups.

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

13. The article of claim 1, wherein each R¹ is independently a methyl moiety.

14. The article of claim 1, wherein v is independently 2 to 4, and wherein both depicted phenylene groups includes an R¹ group located at each ortho ring position, relative to each depicted oxygen atom, that includes only one carbon atom.

15. The article of claim 1, wherein the dihydric phenol comprises hydroquinone, catechol, resorcinol, a substituted variant thereof, or a mixture thereof.

16. The article of claim 7, wherein the dihydric phenol comprises hydroquinone, catechol, resorcinol, or a mixture thereof.

17. The article of claim 1, wherein the polyether polymer includes at least 25% by weight of phenylene groups, and wherein the polyether polymer includes —

CH₂—

CH(OH)—

CH₂—

or —

CH₂—

CH₂—

CH(OH)—

segments.

18. The article of claim 7, wherein the polyether polymer includes at least 45% by weight of phenylene groups.

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

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

C.

21. 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.

22. 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).

23. 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.

24. The article of claim 7, wherein the polyether polymer has a polydispersity index of from 1.5 to 5, the segments of Formula (I) constitute at least 30% by weight of the polyether polymer, and the coating is an interior food-contact coating.

25. The article of claim 1, wherein the polyether polymer has a polydispersity index of from 2 to 3.5, and wherein the diepoxide compound is non-genotoxic.

26. An article comprising a food or beverage container, or a portion thereof, having a metal substrate and an interior food-contact coating applied on at least a portion of the metal substrate;

wherein the coating is substantially free of 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 coating is formed from a liquid thermoset coating composition that includes a polyether polymer prepared from ingredients including;

(i) an extender comprising catechol, hydroquinone, resorcinol, or a mixture thereof, and

(ii) a diepoxide compound that includes a segment of the below Formula (I);

27. A coating composition, comprising:

a polyether polymer that includes at least 25% by weight of aryl or heteroaryl groups and has a glass transition temperature of at least 60°

C. and a number average molecular weight of at least 2,000, 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);