Coating compositions for containers and methods of coating
View Patent ↗This invention provides a coating composition for use on a food-contact surface of a container (e.g., a food or beverage can) that includes a polymer having one or more segments of Formula I: —O—Ar—R n —C(O)—O—R 1 —O—C(O)—R n —Ar—O— wherein each Ar is independently a divalent aryl group (i.e., an arylene group) or heteroarylene group; R 1 is a divalent organic group; each R is independently a divalent organic group; and n is 0 or 1. Containers comprising the polymer and methods of making such containers are also provided.
1. A coating composition comprising a liquid coating composition, wherein the coating composition includes:
a polymer having ether linkages and one or more segments of Formula I:
—O—Ar—R n —C(O)—O—R 1 —O—C(O)—R n —Ar—O—
wherein:
each Ar is independently a divalent aryl group or heteroarylene group;
each R is independently a divalent organic group,
R 1 is a divalent organic group, and
each n is 0 or 1; and
a liquid carrier.
2. The coating composition of claim 1 , wherein the polymer further comprises —CH 2 —CH(OH)—CH 2 — segments.
3. The coating composition of claim 1 , wherein R 1 provides hydrolytic stability to at least one of the adjacent ester linkages.
4. The coating composition of claim 1 , wherein R 1 is —C(R 2 ) 2 —Y t —C(R 2 ) 2 — wherein each R 2 is independently hydrogen or an organic group, each Y is independently a divalent organic group, and t is 0 or 1.
5. The coating composition of claim 4 , wherein Y includes one or more ether or ester linkages.
6. The coating composition of claim 1 , wherein R 1 has the formula —(C(R 2 ) 2 ) s — wherein s is at least 2, wherein each R 2 is independently hydrogen or an organic group.
7. The coating composition of claim 4 , wherein Y is —[Z w —C(R 2 ) 2 —O—C(O)—R 3 —C(O)—O—C(R 2 ) 2 —] v Z w —, wherein w is 0 or 1, v is 1 to 10, each R 2 is as described in claim 4 each R 3 is independently a divalent organic group, and each Z is independently a divalent organic group.
8. The coating composition of claim 7 , wherein each Z provides hydrolytic stability to at least one adjacent ester linkages.
9. The coating composition of claim 1 , wherein each Y provides hydrolytic stability to at least one of the ester linkages adjacent R 1 in Formula I.
10. The coating composition of claim 1 , wherein n is 0.
11. The coating composition of claim 1 , wherein each Ar is independently a phenylene group.
12. The coating composition of claim 11 , wherein each Ar is independently a phenylene group of the formula —C 6 (O 4 —, wherein each R 4 is independently hydrogen, a halogen, or an organic group, wherein two R 4 groups can optionally join to form a ring optionally containing one or more heteroatoms.
13. The coating composition of claim 12 , wherein each R 4 is hydrogen.
14. The coating composition of claim 1 , wherein the coating composition is a water-based system.
15. The coating composition of claim 1 , wherein the coating composition is an organic solvent-based system.
16. The coating composition of claim 1 , wherein the coating composition includes at least 25 weight percent of the polymer having segments of Formula I, based on the non-volatile film-forming components of the coating composition.
17. The coating composition of claim 1 , wherein the coating composition includes at least 50 weight percent of the polymer having segments of Formula I, based on the non-volatile film-forming components of the coating composition.
18. The coating composition of claim 1 , wherein the coating composition is substantially free of BPA, BADGE, BPF, and BFDGE.
19. The coating composition of claim 1 , wherein the polymer has a number average molecular weight of at least 2,000.
20. The coating composition of claim 1 , wherein R 1 includes at least 8 carbon atoms.
21. The coating composition of claim 1 , wherein the polymer comprises a reaction product of a compound of Formula II:
HO—Ar—R n —C(O)—O—R 1 —O—C(O)—R n —Ar—OH,
wherein each Ar, R, R 1 , and n are as described in Formula I.
22. The coating composition of claim 1 , wherein the polymer comprises a reaction product of a non-BPA or non-BPF based diepoxide reacted with a compound of Formula II:
HO—Ar—R n —C(O)—O—R 1 —O—C(O)—R n —Ar—OH,
wherein each Ar, R, R 1 , and n are as described for Formula I.
23. A coating composition, comprising:
a polymer having one or more backbone segments of Formula I:
—O—Ar—R n —C(O)—O—R 1 —O—C(O)—R n —Ar—O—
wherein:
each Ar is independently a divalent phenylene group of the formula —C 6 (R 4 ) 4 —, wherein each R 4 is independently hydrogen, a halogen, or an organic group, wherein two R 4 groups can optionally join to form a ring optionally containing one or more heteroatoms;
each R is independently a divalent organic group;
R 1 is a divalent organic group; and
each n is 0 or 1; and
wherein the polymer, prior to any cure of the coating composition, includes ether linkages.
24. The coating composition of claim 23 , wherein the coating composition includes a liquid carrier comprising water.
25. The coating composition of claim 23 , wherein the polymer comprises a reaction product of a non-BPA or non-BPF based diepoxide reacted with a compound of Formula II:
HO—Ar—R n —C(O)—O—R 1 —O—C(O)—R n —Ar—OH,
wherein each Ar, R, R 1 , and n are as described for Formula I.
26. The coating composition of claim 23 , wherein the polymer further comprises —CH 2 —CH(OH)—CH 2 — segments.
27. The coating composition of claim 23 , wherein the coating composition is substantially free of bound BPA, BADGE, BPF, and BFDGE.
28. A coating composition comprising a liquid coating composition, wherein the coating composition includes:
a polymer having:
ether linkages;
one or more segments of Formula I:
—O—Ar—R n —C(O)—O—R 1 —O—C(O)—R n —Ar—O—
wherein:
each Ar is independently a divalent aryl group or heteroarylene group;
each R is independently a divalent organic group,
R 1 is a divalent organic group, and
each n is 0 or 1; and
—CH 2 —CH(OH)—CH 2 — segments, wherein a —CH 2 —CH(OH)—CH 2 — segment is attached to each of the oxygen atoms depicted in Formula; and
a liquid carrier.