Polymer having polycyclic groups and coating compositions thereof
View Patent ↗A polymer and coating composition containing the polymer are provided that are useful in coating applications such as, for example, food or beverage packaging containers. The polymer preferably includes a backbone having one or more polycyclic groups. In one embodiment, the polymer is a polyester and, more preferably, a polyester-urethane polymer. In one embodiment, the one or more polycyclic groups is a tricyclic or higher group.
1. An article, comprising:
a metal substrate of a food or beverage container, or a portion thereof; and
a coating applied on at least a portion of a major surface of the substrate, the coating prepared from a coating composition including a polyester polymer having a plurality of polycyclic groups, wherein the polymer includes both one or more unsaturated bicyclic groups and one or more at least tricyclic groups.
2. The article of claim 1 , wherein a backbone of the polyester polymer includes both ester and urethane linkages.
3. The article of claim 1 , wherein the one or more unsaturated bicyclic groups are bridged bicyclic groups and wherein a carbon-carbon double bond is present between atoms of a ring of the unsaturated bicyclic group.
4. The article of claim 1 , wherein the one or more unsaturated bicyclic groups comprise bicyclo[2.1.1]hexene, bicyclo[2.2.1]heptene, bicyclo[2.2.1]heptadiene, bicyclo[2.2.2]octene, bicyclo[2.2.2]octadiene, or a combination thereof.
5. The article of claim 1 , wherein the one or more unsaturated bicyclic groups are provided by nadic acid, nadic anhydride, or a mixture thereof.
6. The article of claim 1 , wherein the polycyclic groups are present in a backbone of the polymer.
7. The article of claim 1 , wherein the polymer includes at least 10 weight percent of the polycyclic groups, based on the weight percent of polycyclic-group-containing monomer relative to the total weight of the polymer.
8. The article of claim 1 , wherein the polymer has a glass transition temperature of at least 50° C.
9. The article of claim 1 , wherein the polymer has a glass transition temperature of 80° C. to 125° C.
10. The article of claim 1 , wherein the polymer has an iodine value of at least 10.
11. The article of claim 1 , wherein the one or more at least tricyclic groups are saturated groups.
12. The article of claim 1 , wherein the polymer includes:
from 5 to 50 percent by weight of the one or more at least tricyclic groups,
from 1 to 35 percent by weight of the one or more unsaturated bicyclic groups,
wherein the aforementioned weight percents are based on the amount of at least tricyclic group containing monomer and unsaturated bicyclic group containing monomer incorporated into the polymer relative to the total weight of the polymer.
13. The article of claim 1 , wherein the polymer is derived from ingredients including, based on total weight solids, from 17 to 33 percent by weight of tricyclodecane dimethanol and from 5 to 17 percent by weight of nadic anhydride.
14. The article of claim 1 , wherein the coating composition, based on total weight solids, includes at least 50 weight percent of the polymer.
15. The article of claim 1 , wherein the polymer further comprises one or more polycyclic groups derived from isosorbide, isomannide, isoiodide, or a derivative or combination thereof.
16. The article of claim 1 , wherein the one or more at least tricyclic groups comprise a substituted or unsubstituted tricyclodecane group.
17. The article of claim 16 , wherein the tricyclodecane group is provided by tricyclodecane dimethanol, tricyclodecane diamine, tricyclodecane diisocyanate, or a derivative or mixture thereof.
18. A method, comprising:
providing a coating composition comprising:
a polyester polymer having a plurality of polycyclic groups, wherein the polymer includes one or more unsaturated bicyclic groups and one or more at least tricyclic groups, and
a liquid carrier; and
applying the coating composition on a metal substrate prior to, or after, forming the metal substrate into a food or beverage can or a portion thereof.
19. A coating composition, comprising:
at least 10 weight percent, based on total solids, of a polyester polymer having:
a glass transition temperature of at least 50° C., and
polycyclic groups that constitute at least 10 weight percent of the polymer, based on the weight percent of polycyclic-group-containing monomer relative to the total weight of the polymer, wherein the polymer includes both one or more unsaturated bicyclic groups and one or more at least tricyclic groups;
a resole phenolic type crosslinker; and
a liquid carrier.
20. The coating composition of claim 19 , wherein a backbone of the polyester polymer includes urethane linkages.