Methods and materials for the functionalization of polymers and coatings including functionalized polymer
The disclosure provides a functionalized polymer for use in coating compositions and a method for making the functionalized polymer. In some embodiments, the functionalized polymer is a water-dispersible polymer, more preferably a water-dispersible polyester polymer, having one or more side groups including one or more salt groups. Packaging containers (e.g., food or beverage cans) comprising the functionalized polymer and methods of making such containers are also provided.
1. A method of making a functionalized polyester polymer comprising:
providing an unsaturated precursor polyester polymer having one or more double or triple bonds; and
reacting in a Diels-Alder reaction, an Ene reaction, or a combination thereof:
(i) an unsaturated compound having one or more functional groups with (ii) the unsaturated precursor polyester polymer such that a covalent attachment is formed between the unsaturated compound and the unsaturated precursor polyester polymer;
wherein the one or more functional group comprises an acid group, an isocyanate group, a blocked isocyanate group, a ketone group, or a mixture thereof; and wherein the functionalized polymer includes a backbone having one or more heteroatoms including any combination of condensation and/or step growth linkages selected from the group comprising of: amide, carbonate ester, ester, ether, imide, urea, urethane, or combinations thereof.
2. The method of claim 1 , wherein the unsaturated precursor polyester polymer has a number average molecular weight of at least 4,000.
3. The method of claim 1 , wherein one or both of the unsaturated precursor polyester polymer and the unsaturated compound include conjugated carbon-carbon double bonds.
4. The method of claim 1 , wherein the functionalized polyester polymer resulting from the method has a glass transition temperature of at least 25° C.
5. The method of claim 4 , wherein the functionalized polyester polymer resulting from the method comprises a water-dispersible polymer.
6. The method of claim 1 , wherein the functionalized polyester polymer resulting from the method includes a plurality of the side groups and at least one of the side groups is a Diels-Alder reaction product and at least one of the side groups is an Ene reaction product.
7. The functionalized polyester polymer resulting from the method of claim 6 .
8. A method of making a functionalized polymer comprising:
providing an unsaturated precursor polymer having a number average molecular weight of at least 2,000 and one or more double or triple bonds; and
reacting in a Diels-Alder reaction, an Ene reaction, or a combination thereof: (i) an unsaturated compound having one or more functional groups with (ii) the unsaturated precursor polymer such that a covalent attachment is formed between the unsaturated compound and the unsaturated precursor polymer, wherein the unsaturated compound comprises sorbic acid or neutralized sorbic acid.
9. The method of claim 1 , wherein the functionalized polyester polymer resulting from the method has a glass transition temperature of less than about 150° C.
10. The method of claim 1 , wherein the functionalized polyester polymer resulting from the method has a glass transition temperature of less than about 100° C.
11. The method of claim 1 , wherein the functionalized polyester polymer has a number average molecular weight of at least 5,000.
12. The method of claim 1 , wherein the functionalized polyester polymer has a number average molecular weight of greater than about 10,000 to less than about 30,000.
13. The method of claim 1 , wherein the unsaturated compound has an acid number of at least 40 mg KOH per gram resin.
14. The method of claim 9 , wherein the unsaturated compound has an acid number of at least 40 to no greater than 100 mg KOH per gram resin.
15. The method of claim 1 , wherein the functionalized polyester polymer resulting from the method is an aromatic polyester polymer.
16. The method of claim 1 , wherein the functionalized polyester polymer resulting from the method is an aromatic polyester polymer that includes at least 10 wt-% of aromatic groups.
17. The method of claim 1 , wherein the functionalized polyester polymer is water-dispersible.
18. The method of claim 1 , wherein the unsaturated polyester precursor includes one or more unsaturated structural units provided by maleic acid or maleic anhydride.