Compositions for containers and other articles and methods of using same

Patent metadata

Field	Value
Publication number	US-10294388-B2
Application number	US-201615204559-A
Country	US
Kind code	B2
Filing date	Jul 7, 2016
Priority date	Feb 7, 2011
Publication date	May 21, 2019
Grant date	May 21, 2019

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.

First claim

What is claimed is:

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

Assignees

• Swimc Llc

Inventors

• Niederst Jeffrey
• Evans Richard H
• O'Brien Robert M
• Romagnoli Kevin
• Von Maier Mark S

Classifications

• B05D7/227 Primary

  of containers, cans or the like · CPC title

• Y10T428/1355

  Elemental metal containing [e.g., substrate, foil, film, coating, etc.] · CPC title

• C09D5/033

  characterised by the additives · CPC title

• C09D5/08

  Anti-corrosive paints · CPC title

• C09D5/037

  Rheology improving agents, e.g. flow control agents · CPC title