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 method of making a polymer, comprising:
providing a compound of Formula II:
HO—Ar—R n —C(O)—O—R 1 —O—C(O)—R n —Ar—OH,
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
n is 0 or 1; and
reacting the compound of Formula II with a BPA- or BPF-free diepoxide having one or more ether linkages to form a polymer.
2. The method of claim 1 , wherein the BPA- or BPF-free diepoxide comprises a condensation reaction product of a dihydroxy compound and epichlorohydrin.
3. The method of claim 1 , wherein the compound of Formula II is the esterification reaction product of one mole of a diol with two moles of an acid.
4. The method of claim 3 , wherein the diol is 1,4-cyclohexane dimethanol, neopentyl glycol, 2-butyl-2-ethyl-1,3-propane diol, or 2-methyl-1,3-propane diol.
5. The method of claim 4 , wherein the acid is 4-hydroxy benzoic acid.
6. The method of claim 1 , wherein the compound of Formula II comprises the transesterification reaction product of one mole of a diol with two moles of an ester.
7. The method of claim 6 , wherein the diol is 1,4-cyclohexane dimethanol, neopentyl glycol, 2-butyl-2-ethyl-1,3-propane diol, or 2-methyl-1,3-propane diol, and the ester is 4-hydroxy methyl benzoate, 4-hydroxy ethyl benzoate, or 4-hydroxy butyl benzoate.
8. The method of claim 1 , wherein each Ar is independently a phenylene group.
9. The method of claim 1 , wherein each Ar is independently a 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.
10. The method of claim 1 , wherein R 1 includes at least 3 carbon atoms.
11. The method of claim 1 , wherein R 1 includes at least 8 carbon atoms.
12. The method of claim 1 , wherein R 1 provides hydrolytic stability to at least one of the adjacent ester linkages.
13. The method of claim 1 , wherein R 1 is —C(R 2 ) 2 —Y t —C(R 2 ) 2 —, and wherein each R 2 is independently hydrogen or an organic group, Y is a divalent organic group, and t is 0 or 1.
14. The method of claim 13 , wherein Y includes one or more ether or ester linkages.
15. The method 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.
16. The method of claim 1 , wherein n is 0.
17. The method of claim 1 , wherein the polymer has a number average molecular weight of at least 2,000.
18. The method of claim 1 , wherein the polymer is epoxy or phenoxy terminated.
19. The method of claim 1 , wherein the polymer is a water-dispersible polymer.
20. The method of claim 1 , wherein the polymer is substantially free of BPA, BADGE, BPF, and BFDGE.
21. A method of making a polymer, comprising:
providing a compound of Formula II:
HO—Ar—R n —C(O)—O—R 1 —O—C(O)—R n —Ar—OH,
wherein:
each Ar is independently a phenylene group;
each R is independently a divalent organic group;
R 1 is a divalent organic group; and
n is 0 or 1; and
reacting the compound of Formula II with a BPA- or BPF-free diepoxide to form a polymer, wherein the BPA- or BPF-free diepoxide includes one or more ether linkages and is a condensation product of a dihydroxy compound and epichlorohydrin.