IP Library Granted Patent US 10,294,388
Granted Patent B2
US 10,294,388 · App. 15/204,559 · Granted May 21, 2019

Compositions for containers and other articles and methods of using same

Inventors: Jeffrey Niederst (Leechburg, PA); Richard H. Evans (Wexford, PA); Robert M. O'Brien (Monongahela, PA); Kevin Romagnoli (Pittsburgh, PA); Mark S. Von Maier (Harmony, PA)
Assignee: SWIMC LLC
C09D163/00B05D7/227B21D5/00B65D25/14C09D5/03C09D5/031C09D5/033C09D5/037C09D5/08B05D2202/00C08G59/00C08G65/00Y10T428/1355
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Quick Facts
Patent No.
US 10,294,388
App. No.
15/204,559
Granted
May 21, 2019
Kind
B2
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 (63)

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):

wherein:

each of the oxygen atoms depicted in Formula (I) is present in an ether linkage;

each R 1 is free of halogen atoms and is independently a carbon-containing group or a sulfur-containing group;

v is independently 0 to 4;

w is 4;

R 2 is an organic group that includes only 1 carbon atom or at least 8 carbon atoms, wherein R 2 includes a carbon atom that is attached to a carbon atom of each of the phenylene groups depicted in Formula (I), with the proviso that if R 2 includes only 1 carbon atom then each depicted phenylene group includes at least one R 1 group that includes 1 or 2 carbon atoms and is located at an ortho ring position relative to the depicted oxygen atom;

n is 1;

t is 1; and

R 1 if present, can join with one or more other R 1 groups and/or R 2 to form one or more cyclic groups.

2. The article of claim 1 , wherein R 2 is —CH 2 —.

3. The article of claim 1 , wherein R 2 includes at least 10 carbon atoms.

4. The article of claim 1 , wherein R 2 includes at least 12 carbon atoms.

5. The article of claim 1 , wherein R 2 includes 8 to 15 carbon atoms.

6. The article of claim 1 , wherein R 2 includes 10 to 15 carbon atoms.

7. The article of claim 1 , wherein R 2 has an atomic weight of less than 500 Daltons.

8. The article of claim 1 , wherein R 2 includes at least 8 carbon atoms and includes one or more cyclic groups.

9. The article of claim 8 , wherein the carbon atom of R 2 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 R 2 .

13. The article of claim 1 , wherein each R 1 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 R 1 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 —CH 2 —CH(OH)—CH 2 — or —CH 2 —CH 2 —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):

wherein:

each of the oxygen atoms depicted in Formula (I) is present in an ether linkage;

each R 1 is free of halogen atoms and is independently a carbon-containing group or a sulfur-containing group that;

v is independently 0 to 4;

w is 4;

R 2 is an organic group that includes only 1 carbon atom or at least 8 carbon atoms, wherein R 2 includes a carbon atom that is attached to a carbon atom of each of the phenylene groups depicted in Formula (I), with the proviso that if R 2 includes only 1 carbon atom then each depicted phenylene group includes at least one R 1 group that includes 1 or 2 carbon atoms and is located at an ortho ring position relative to the depicted oxygen atom;

n is 1;

t is 1; and

R 1 , if present, can join with one or more other R 1 groups and/or R 2 to form one or more cyclic groups.

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):

wherein:

each of the oxygen atoms depicted in Formula (I) is present in an ether linkage;

each R 1 is free of halogen atoms and is independently a carbon-containing group or a sulfur-containing group;

v is independently 0 to 4;

w is 4;

R 2 is an organic group that includes only 1 carbon atom or at least 8 carbon atoms, wherein R 2 includes a carbon atom that is attached to a carbon atom of each of the phenylene groups depicted in Formula (I), with the proviso that if R 2 includes only 1 carbon atom then each depicted phenylene group includes at least one R 1 group that includes 1 or 2 carbon atoms and is located at an ortho ring position relative to the depicted oxygen atom;

n is 1;

t is 1; and

R 1 , if present, can join with one or more other R 1 groups and/or R 2 to form one or more cyclic groups; and

a liquid carrier;

wherein the coating composition is a thermoset food or beverage can coating composition suitable for use in forming an interior food-contact can coating, and wherein the coating composition 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.

Assignments (8)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 6, 2023
From: THE SHERWIN-WILLIAMS HEADQUARTERS COMPANY
To: SWIMC LLC
Reel/Frame 063275/0494 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 11, 2022
From: THE SHERWIN-WILLIAMS COMPANY
To: THE SHERWIN-WILLIAMS HEADQUARTERS COMPANY
Reel/Frame 060366/0979 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 30, 2021
From: THE VALSPAR CORPORATION
To: THE SHERWIN-WILLIAMS COMPANY
Reel/Frame 057204/0946 →
MERGER Recorded Oct 29, 2020
From: ENGINEERED POLYMER SOLUTIONS, INC.
To: THE VALSPAR CORPORATION
Reel/Frame 054443/0772 →
MERGER Recorded Sep 2, 2020
From: VALSPAR SOURCING, INC.
To: ENGINEERED POLYMER SOLUTIONS, INC.
Reel/Frame 053826/0606 →
NUNC PRO TUNC ASSIGNMENT Recorded Mar 24, 2020
From: THE SHERWIN-WILLIAMS COMPANY
To: VALSPAR SOURCING, INC.
Reel/Frame 052217/0640 →
CORRECTIVE ASSIGNMENT TO CORRECT THE INCORRECT PATENT NO. 8465946 PREVIOUSLY RECORDED AT REEL: 045281 FRAME: 0529. ASSIGNOR(S) HEREBY CONFIRMS THE MERGER. Recorded May 4, 2018
From: VALSPAR SOURCING, INC.
To: THE SHERWIN-WILLIAMS COMPANY
Reel/Frame 046087/0150 →
MERGER Recorded Feb 8, 2018
From: VALSPAR SOURCING. INC
To: THE SHERWIN-WILLIAMS COMPANY
Reel/Frame 045281/0529 →
Continuity (6)
Continuation 13570632 · Aug 9, 2012
Continuation In Part PCTUS2012024191 · Feb 7, 2012
Continuation In Part PCTUS2012024193 · Feb 7, 2012
Provisional Application 61579072 · Dec 22, 2011
Provisional Application 61440085 · Feb 7, 2011
Related Publication 20170029657A1 · Feb 2, 2017
Cited By (2)
US 12,234,371 US 12,351,677