Polyester-based coating composition for metal substrates
View Patent ↗The present invention provides novel packaging articles, e.g., food and beverage cans, having a novel coating composition applied to at least a portion of a surface thereon. In preferred embodiments, the coating composition includes at least a film-forming amount of a copolyester resin having a backbone that includes one or more soft segments and a plurality of hard segments. The copolyester resin preferably has a glass transition temperature from about from about 10° C. to about 50° C. The present invention also provides a method for making coated articles.
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, wherein the coating composition includes:
a copolyester resin having a glass transition temperature from 10° C. to 50° C. and a backbone that includes a non-random distribution of alternating hard and soft segments connected to one another via step-growth linkages, wherein the hard segments are provided by a cyclic-group-containing polyester oligomer or polymer having a number average molecular weight of at least 500 and the soft segments are provided by an aliphatic reactant, and wherein the copolyester resin is formed by reacting the polyester oligomer or polymer with the aliphatic reactant; and
a crosslinker.
2. The article of claim 1 , wherein the copolyester resin has a glass transition temperature from 15° C. to 35° C.
3. The article of claim 1 , wherein the soft segment comprises a substituted or unsubstituted hydrocarbon segment having at least four backbone carbon atoms.
4. The article of claim 1 , wherein the soft segment comprises a linear hydrocarbon moiety that includes 6 to 36 carbon atoms.
5. The article of claim 1 , wherein the aliphatic reactant comprises adipic acid, azelaic acid, a fatty-acid-based diacid, sebacic acid, succinic acid, glutaric acid, or a derivative or mixture thereof.
6. The article of claim 1 , wherein the copolyester resin is a reaction product of reactants including: a hydroxyl-functional polyester oligomer or polymer, and a diacid or diacid equivalent, wherein the weight ratio of polyester oligomer or polymer to diacid or diacid equivalent is from 8:1 to 20:1.
7. The article of claim 1 , wherein the coating composition includes, based on total resin solids, at least 60 weight percent of the copolyester resin.
8. The article of claim 1 , wherein the coating composition further comprises, based on total resin solids, from 2 to 20 weight percent of an acrylate copolymer.
9. The article of claim 1 , wherein the copolyester resin has an acid number less than 10 and a hydroxyl number of from 10 to 50.
10. The article of claim 1 , wherein the copolyester resin constitutes greater than 90 weight percent of the total amount of polyester present in the coating composition, based on total polyester solids.
11. The article of claim 1 , wherein the coating composition is substantially free of bound bisphenol A and aromatic glycidyl ether compounds.
12. The article of claim 1 , wherein the article includes a riveted beverage can end having the coating composition applied on at least a portion of the can end.
13. The article of claim 1 , wherein the step-growth linkages are ester linkages.
14. The article of claim 1 , wherein the hard segments constitute at least 75 wt-% of the polymer.
15. The article of claim 14 , wherein cyclic groups constitute at least 20 wt-% of the hard segments.
16. The article of claim 1 , wherein cyclic groups constitute at least 50 wt-% of the hard segments.
17. The article of claim 1 , wherein the polyester oligomer or polymer has a number average molecular weight of at least 1,000 and a Tg of at least 20° C.
18. The article of claim 16 , where the polyester oligomer or polymer has a Tg of from 20° C. to 40° C.
19. The article of claim 1 , wherein the polyester oligomer or polymer is formed from monomers including isophthalic acid and terephthalic acid.
20. The article of claim 1 , wherein the aliphatic reactant comprises a compound having the structure R 3 —(CR 4 2 ) t —R 3 , wherein:
each R 3 is a carboxylic group or equivalent thereof,
t is 4 to 60; and
each R 4 is independently a hydrogen, a halogen, or an organic group.
21. The article of claim 1 , wherein the cured coating has a Tg of at least 20° C. to less than about 80° C.