Compositions for containers and other articles and methods of using same

• US 10,435,199 B2
• Filed: 08/07/2018
• Issued: 10/08/2019
• Est. Priority Date: 08/09/2012
• Status: Active Grant

• Current Assignee: Swimc, LLC (The Sherwin-Williams Company)
• Original Assignee: Swimc, LLC (The Sherwin-Williams Company)
• Inventors: Niederst, Jeffrey, Evans, Richard H., O'Brien, Robert M., Romagnoli, Kevin, Von Maier, Mark S.
• Primary Examiner(s): Boykin, Terressa
• Application Number:
  US16/057,469
• Publication Number:
  US 20180346199A1
• Time in Patent Office: 427 Days
• Field of Search: 428 358
• 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: B65D 81/34 for packaging foodstuffs or other articles intended to be cooked or heated within the package
• CPC Class Codes: C08G 65/2612 containing aromatic or arylaliphatic hydroxyl groups
• CPC Class Codes: C09D 163/00 Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• CPC Class Codes: C09D 171/00 Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain based on polyacetals C09D159/00; based on epoxy resins C09D163/00; based on polythioether-ethers C09D181/02; based on polyethersulfones C09D181/06; Coating compositions based on derivatives of such polymers
• CPC Class Codes: C09D 171/12 Polyphenylene oxides
• 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, the coating composition comprising;

a polyether polymer that includes at least 25% by weight of aryl or heteroaryl groups, wherein the coating composition contains less than 1,000 parts per million (ppm) 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;

wherein the polyether polymer is formed by reacting ingredients including;

(i) an extender and (ii) a diepoxide compound, wherein the extender or diepoxide compound, or both, includes one or more segments of the below Formula (I);

2. The article of claim 1, wherein the polyether polymer includes at least 25% by weight of phenylene groups, t is 1 and each of the phenylene groups depicted in Formula (I) includes two Hydrogen atoms attached to the ring at an ortho position relative to the depicted oxygen atom.

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 t is 1, n is 1, and R² is an organic group having 8 or more carbon atoms.

5. The article of claim 1, wherein t is 1, n is 1, and R² is a segment of the structure —

C(R⁷)(R⁸)—

, wherein R⁷ and R⁸ are each independently a hydrogen atom, a halogen atom, an organic group, a sulfur-containing group, or a nitrogen-containing group, and wherein R⁷ and R⁸ can optionally join to form a cyclic group, with the proviso that R⁷ and R⁸ are not both —

CH₃.

6. The article of claim 5, wherein R² has an atomic weight greater than 200 Daltons.

7. The article of claim 1, wherein t is 1, n is 1, and the ether oxygen atom of each phenylene group depicted in Formula (I) is located at a para position relative to R².

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

9. The article of claim 1, wherein the diepoxide compound includes one or more segments of Formula (I).

10. The article of claim 9, wherein the extender comprises hydroquinone, catechol, resorcinol, or a substituted variant thereof.

11. The article of claim 1, wherein the polyether polymer that has a Tg of at least 30°

C. prior to cure of the coating composition and includes at least 25 percent by weight of phenylene groups.

12. The article of claim 1, wherein the coating composition comprises at least 10 weight percent, based on the total resin solids of the coating composition, of a polyether polymer having a number average molecular weight of at least 2,000.

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

C. prior to cure of the coating composition.

14. The article of claim 1, wherein the diepoxide compound is not genotoxic and is derived from a dihydric phenol that includes a segment of Formula (I) and exhibits a log Relative Proliferative Effect value in the MCF-7 cell proliferation assay of less than −

3.

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

16. The article of claim 1, wherein R² includes a polar group.

17. The article of claim 16, wherein the polar group comprises a group selected from a ketone, a carboxyl, a carbonate, a hydroxyl, a phosphate, a sulfoxide, or a combination thereof.

18. The article of claim 1, wherein t is 1, n is 1, and each v is 0.

19. The article of claim 18, wherein:

the polyether polymer has a glass transition temperature of at least 30°

C. prior to cure of the coating composition and a number average molecular weight of at least 2,000;

the segment of Formula (I) has an atomic weight of less than 600 Daltons; and

each of the oxygen atoms depicted in Formula (I) are present in an ether linkage.

20. The article of claim 19, wherein the extender includes one or more segments of Formula (I) and the diepoxide is an aliphatic diepoxide.

21. The article of claim 19, wherein R² has one or both of:

(i) an atomic weight greater than 200 Daltons or (ii) a polar group selected from a ketone, a carboxyl, a carbonate, a hydroxyl, a phosphate, a sulfoxide, or a combination thereof.

22. The article of claim 1, wherein a mono-layer or multi-layer coating including a layer formed from the coating composition has an overall average dry coating thickness of from about 2 to about 15 microns.

23. The article of claim 1, wherein the polyether polymer does not include any structural units derived from a dihydric phenol that exhibit an estrogenic agonist activity greater than 4,4′

-(propane-2,2-diyl)bis(2,6-dibromophenol) in the MCF-7 assay.

24. The article of claim 1, wherein the extender includes one or more segments of Formula (I) and the diepoxide is an aliphatic diepoxide;

and wherein the polyether polymer has a number average molecular weight of at least 4,000 and a Tg of at least 80°

C.

25. The article of claim 1, wherein the polyether polymer does not include any structural units derived from a dihydric phenol that exhibit an estrogenic agonist activity greater than 4,4′

-(propane-2,2-diyl)bis(2,6-dibromophenol) in the MCF-7 assay.

26. The article of claim 1, wherein the polyether polymer includes at least 25% by weight of phenylene groups, t is 1 and each of the phenylene groups depicted in Formula (I) includes two Hydrogen atoms attached to the ring at an ortho position relative to the depicted oxygen atom;

and wherein the extender comprises hydroquinone, catechol, resorcinol, or a substituted variant thereof.

27. The article of claim 1, wherein the diepoxide compound is not genotoxic and is derived from a dihydric phenol that includes a segment of Formula (I) and exhibits a log Relative Proliferative Effect value in the MCF-7 cell proliferation assay of less than −

3.

28. A method comprising:

providing a metal substrate; and

applying on at least a portion of the substrate a coating composition comprising a polyether polymer that includes at least 25% by weight of aryl or heteroaryl groups, wherein the coating composition contains less than 1,000 parts per million (ppm) 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;

wherein the polyether polymer is formed by reacting ingredients including;

(i) an extender and (ii) a diepoxide compound, wherein the extender or diepoxide compound, or both, includes one or more segments of the below Formula (I);

29. The method of claim 28, further comprising:

causing the metal substrate to be formed into a food or beverage container or a portion thereof.

30. The method of claim 28, wherein the metal substrate is formed into a beverage can end.

31. The method of claim 28, wherein the coating composition is spray applied onto an interior surface of a metal food or beverage can that includes a body portion and a bottom end portion.

32. The method of claim 28, wherein the coating composition is a solvent-based coating composition.

33. The method of claim 28, wherein the coating composition is a water-based coating composition.