Polymer having unsaturated cycloaliphatic functionality and coating compositions therefrom
View Patent ↗A polymer is provided that preferably includes at least one unsaturated cycloaliphatic group. In one embodiment, the polymer is combined with an optional crosslinker and an optional carrier to form a coating composition suitable for use in coating articles such as packaging articles. In one embodiment, the polymer has at least one unsaturated cycloaliphatic group that is at least bicyclic.
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 surface of the metal substrate, wherein the coating is formed from a coating composition comprising a polyester polymer having a backbone or pendant unsaturated monocyclic cycloaliphatic group.
2. The article of claim 1 , wherein the unsaturated monocyclic cycloaliphatic group includes a substituted or unsubstitituted C3-C13 ring.
3. The article of claim 1 , wherein the unsaturated monocyclic cycloaliphatic group includes a substituted or unsubstitituted C4-C9 ring.
4. The article of claim 1 , wherein the unsaturated monocyclic cycloaliphatic group comprises a substituted or unsubstituted: cyclobutene, cyclopentene, cyclopentadiene, cyclohexene, cyclohexadiene, cycloheptene, cycloheptadiene, cyclooctene, cyclooctadiene, cyclononene, cyclodecene, cyclodecadiene, cycloundecene, cyclododecenes, cyclotridecene, or cyclononadiene.
5. The article of claim 1 , wherein the unsaturated monocyclic cycloaliphatic group comprises a substituted or unsubstituted group selected from cyclopropene, cyclobutene, trans-cyclooctene, trans-cyclononene, cyclobutadiene, cyclopentadiene, 1,3-cyclohexadiene, 1,3-cycloheptadiene, 1,3 cyclooctadiene, 1,3 cyclononadiene, or 1,3-cyclodecadiene.
6. The article of claim 1 , wherein the unsaturated monocyclic cycloaliphatic group has a ring that includes 3 to 5 atoms.
7. The article of claim 1 , wherein the unsaturated monocyclic cycloaliphatic group has a ring that includes 3 to 4 atoms.
8. The article of claim 1 , wherein the unsaturated monocyclic cycloaliphatic group has at least one double bond with a heat of hydrogenation greater than that of cyclohexene.
9. The article of claim 1 , wherein the unsaturated monocyclic cycloaliphatic group has at least one double bond with a heat of hydrogenation at least about as high as that of bicyclo[2.2.2]octene.
10. The article of claim 1 , wherein the unsaturated monocyclic cycloaliphatic group includes at least one carbon-carbon bond located between atoms of a ring.
11. The article of claim 1 , wherein the polyester polymer includes a plurality of backbone unsaturated monocyclic cycloaliphatic groups.
12. The article of claim 1 , wherein the polyester polymer has an iodine value of at least about 10.
13. The article of claim 1 , wherein the polyester polymer has a Tg of at least 20° C.
14. The article of claim 1 , wherein the polyester polymer includes less than 3 weight percent of fatty acids and oils, based on the total non-volatile weight of ingredients used to make the polyester polymer.
15. The article of claim 1 , wherein the polyester polymer includes less than 1 weight percent of long-chain hydrocarbons including eight or more carbon atoms, based on the total non-volatile weight of ingredient used to make the polyester polymer.
16. The article of claim 1 , wherein unsaturated monocyclic cycloaliphatic groups constitute at least about 5 weight percent of the polyester polymer.
17. The article of claim 1 , wherein the polyester polymer is an aromatic polyester polymer that includes at least 20 weight percent of aromatic groups.
18. The article of claim 1 , wherein the polyester polymer includes one or more step-growth linkages other than ester linkages.
19. The article of claim 1 , wherein the unsaturated monocyclic cycloaliphatic group includes at least one allylic hydrogen.
20. An article comprising:
a metal substrate of a food or beverage can or a portion thereof; and
a coating applied on at least a portion of an interior surface of the metal substrate, wherein the coating is formed from a coating composition comprising a liquid carrier and an aromatic polyester polymer having a backbone unsaturated monocyclic cycloaliphatic group, wherein the polyester polymer has a Tg of at least 0° C. and optionally includes one or more step-growth linkages other than ester linkages.