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. A coating composition comprising a water-based varnish that includes a water-dispersible polyester polymer having salt groups and a backbone or pendant unsaturated at least bicyclic group with a double bond located between carbon atoms of a ring.
2. The coating composition of claim 1 , wherein the unsaturated at least bicyclic group comprises a structure represented by the nomenclature expression:
bicyclo[x,y,z]alkene;
wherein:
x is 2 or more,
y and z are each at least 1, and
the term “alkene” denotes that the bicyclic group includes one or more carbon-carbon double bonds.
3. The coating composition of claim 2 , wherein the unsaturated at least bicyclic group comprises 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.
4. The coating composition of claim 1 , wherein the unsaturated at least bicyclic group was incorporated into the polymer using nadic acid, methyl-nadic acid, or an anhydride ahydride or derivative thereof.
5. The coating composition of claim 1 , wherein the polyester polymer includes a plurality of the unsaturated at least bicyclic groups that constitute at least about 5 weight percent of the polyester polymer.
6. The coating composition of claim 1 , wherein the polyester polymer has an iodine value of at least about 10.
7. The coating composition of claim 1 , wherein the polyester polymer has a Tg of at least 25° C.
8. The coating composition of claim 1 , wherein the polyester polymer has an acid number of at least 15.
9. The coating composition of claim 1 , wherein the salt groups comprise neutralized acid or anhydride groups.
10. The coating composition of claim 1 , wherein the polyester polymer includes at least 5 weight percent of aromatic groups.
11. The coating composition of claim 1 , wherein the polyester polymer comprises a reaction product of ingredients including one or more of maleic acid or anhydride, and wherein a structural unit derived from maleic acid or anhydride includes the unsaturated at least bicyclic group.
12. The coating composition of claim 11 , wherein the structural unit is a Diels-Alder reaction product.
13. The coating composition of claim 1 , wherein the polyester polymer is formed from reactants including a dianhydride.
14. The coating composition of claim 13 , wherein the dianhydride comprises pyromellitic dianhydride.
15. The coating composition of claim 1 , wherein the coating composition includes a crosslinker.
16. The coating composition of claim 15 , wherein the crosslinker comprises a resole phenolic crosslinker.
17. A coating composition, wherein the coating composition includes:
50 to 95 weight percent, based on nonvolatile weight, of a water-dispersible aromatic polyester polymer having a backbone or pendant unsaturated at least bicyclic group with a double bond located between carbon atoms of a ring; and
5 to 50 weight percent, based on nonvolatile weight, of a resole phenolic crosslinker; and
a liquid carrier that comprises at least 50 weight percent of water.
18. The coating composition of claim 17 , wherein the unsaturated at least bicyclic group was incorporated into the polymer using nadic acid, methyl-nadic acid, or an anhydride or derivative thereof.
19. The coating composition of claim 18 , wherein the polyester polymer is formed from reactants including a dianhydride.
20. A method, comprising:
providing a water-based varnish that includes a water-dispersible polyester polymer having salt groups and a backbone or pendant unsaturated at least bicyclic group with a double bond located between carbon atoms of a ring; and
applying the coating composition to at least a portion of a metal substrate of a food or beverage can or a portion thereof.