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 aromatic polyester polymer having an unsaturated cycloaliphatic group with a double bond located between carbon atoms of a ring and a number average molecular weight of at least 3,000, wherein the polyester polymer comprises a reaction product of a dianhydride and a polyester polyol having a number average molecular weight of about 500 to about 5,000, and wherein the polymer is completely free of bound BPA and aromatic glycidyl ether compounds.
2. The polyester polymer of claim 1 , wherein the molar ratio of polyester polyol to dianhydride is from about 15:1 to about 25:1.
3. The polyester of claim 1 , wherein the polyester polyol is a reaction product of ingredients including nadic acid, nadic anhydride, methyl-nadic acid, methyl-nadic anhydride, or a mixture thereof.
4. The polyester of claim 1 , wherein the polyester has a glass transition temperature of at least 25° C. to 130° C.
5. The polyester polymer of claim 1 , wherein the polymer is not an alkyd and includes less than 3 weight percent, if any, of fatty acids and oils, based on the total non-volatile weight of ingredients used to make the polymer.
6. The polyester polymer of claim 1 , wherein unsaturated cycloaliphatic groups constitute at least 30 weight percent of the polymer.
7. The polyester polymer of claim 1 , wherein the unsaturated cycloaliphatic groups are bicyclic, tricyclic, or higher order polycyclic groups.
8. The polyester polymer of claim 1 , wherein the polymer includes one or more backbone urethane linkages.
9. The polyester polymer of claim 1 , wherein the polymer has an iodine value of at least 35.
10. The polyester polymer of claim 1 , wherein the unsaturated cycloaliphatic group has a heat of hydrogenation that is at least as high as that of bicyclo[2.2.2]octane.
11. The polyester polymer of claim 1 , wherein the unsaturated cycloaliphatic comprises an unsaturated cycloaliphatic group that has at least one carbon-carbon double bond with a heat of hydrogenation greater than that of cyclohexene.
12. The polyester polymer of claim 1 , wherein a backbone of the polymer is free of urethane linkages and other non-ester step-growth linkages.
13. The polyester polymer of claim 1 , wherein the unsaturated cycloaliphatic group comprises a Diels-Alder reaction product of a structural unit derived from maleic acid or anhydride and cyclopentadiene or dicylcopentadiene.
14. The polyester polymer of claim 1 , wherein a backbone of the polymer is hydroxyl-terminated.
15. The polyester polymer of claim 1 , wherein the polymer is water-dispersible.
16. The polyester polymer of claim 1 , wherein the molar ratio of polyester polyol to dianhydride is from about 5:1 to about 50:1.
17. The polyester polymer of claim 16 , wherein the dianhydride is pyromellitic dianhydride.
18. The polyester of claim 16 , wherein the polyester polyol is a reaction product of ingredients including nadic anhydride.
19. The polyester polymer of claim 16 , wherein the polymer includes less than 1 weight percent, if any, of long-chain hydrocarbons including eight or more carbon atoms, based on the total non-volatile weight of ingredient used to make the polymer.
20. The polyester polymer of claim 16 , wherein unsaturated cycloaliphatic groups constitute at least 5 weight percent of the polymer.
21. The polyester polymer of claim 16 , wherein unsaturated cycloaliphatic groups are bicyclic, tricyclic, or higher order polycyclic groups and constitute at least 5 weight percent of the polyester polymer.
22. The polyester polymer of claim 16 , wherein the polymer has an iodine value of at least 10.
23. A polyester polymer having a glass transition temperature of at least 25° C., a number average molecular weight of at least 3,000, a hydroxyl-terminated backbone, and an unsaturated bicyclic group having a double bond located between carbon atoms of a ring, wherein:
the polymer comprises a reaction product of a dianhydride and a polyester polyol having a number average molecular weight of about 500 to about 5,000,
the molar ratio of polyester polyol to dianhydride is from about 5:1 to about 50:1, and
the polymer is completely free of bound BPA and aromatic glycidyl ether compounds.
24. The polyester polymer of claim 23 , wherein the dianhydride comprises pyromellitic dianhydride and the polymer is water-dispersible.
25. A method of forming a polyester polymer, comprising reacting a dianhydride and a polyester polyol having a number average molecular weight of about 500 to about 5,000 to form a polymer having an unsaturated cycloaliphatic group with a double bond located between carbon atoms of a ring and a number average molecular weight of at least 3,000, wherein the molar ratio of polyester polyol to dianhydride is from about 5:1 to about 50:1, and wherein the polymer is completely free of bound BPA and aromatic glycidyl ether compounds.
26. The method of claim 25 , wherein the dianhydride comprises pyromellitic dianhydride.
27. The method of claim 25 , wherein the polyester polymer is an aromatic polyester polymer that has a glass transition temperature of at least 25° C.
28. The method of claim 27 , wherein the unsaturated cycloaliphatic group is bicyclic, tricyclic, or a higher order polycyclic group.