Polycyclocarbonate compounds and polymers and compositions formed therefrom
Polycyclocarbonate compounds and upgraded molecular weight polymers made from such compounds are provided. The polymers have particular utility in coating compositions, especially for use on food and beverage contact substrates that are formed into or will be formed into containers or container components.
1. An article comprising:
a food or beverage container, or a portion thereof, having a metal substrate and a coating composition applied on at least a portion of the metal substrate, wherein the coating composition includes a polymer that is a reaction product of ingredients including: (i) an extender having at least two functional groups reactive with a cyclocarbonate group and (ii) a polycyclocarbonate compound; and
wherein the polycyclocarbonate compound includes a cyclic group other than a cyclocarbonate group, wherein the cyclic group comprises an alicyclic group; and wherein the alicyclic group comprises a cyclobutane group.
2. The article of claim 1 , wherein the cyclic group comprises a polycyclic group.
3. An article comprising: a food or beverage container, or a portion thereof, having a metal substrate and a coating composition applied on at least a portion of the metal substrate, wherein the coating composition includes a polymer that is a reaction product of ingredients including: (i) an extender having at least two functional groups reactive with a cyclocarbonate group and (ii) a polycyclocarbonate compound; and
wherein the extender comprises a dihydric phenol.
4. The article of claim 3 , wherein the polycyclocarbonate compound is a dicyclocarbonate compound, and wherein the two cyclocarbonate groups of the dicyclocarbonate compound each include a 5-member carbonate-containing ring.
5. The article of claim 4 , wherein the polycyclocarbonate compound has a molecular weight of less than 1,000 Daltons.
6. The article of claim 3 , wherein the polycyclocarbonate compound is derived from a diepoxide of a diol containing a cyclic group.
7. The article of claim 3 , wherein the polycyclocarbonate compound is free of ester linkages.
8. The article of claim 3 , wherein the extender includes an aryl or heteroaryl group and has a molecular weight of less than 1,000 Daltons.
9. The article of claim 3 , wherein the dihydric phenol comprises substituted or unsubstituted: hydroquinone, resorcinol, catechol, or a combination thereof.
10. The article of claim 3 , wherein the polymer comprises a polyether polymer.
11. article of claim 10 , wherein the polyether polymer has a glass transition temperature of at least 40° C. and a number average molecular weight of at least 2,000.
12. The article of claim 10 wherein the polyether polymer includes at least 25% by weight of aryl or heteroaryl groups.
13. The article of claim 10 , wherein the polyether polymer is free of structural units derived from a bisphenol or a diepoxide of a bisphenol.
14. The article of claim 3 , wherein the polycyclocarbonate compound has a structure of the below Formula (II):
wherein:
X is a divalent group;
each R 2 is independently hydrogen, oxygen, a carbon-containing group, a sulfur-containing group, an oxygen-containing group, a nitrogen-containing group, or a phosphorus-containing group;
each n is independently 2 to 13;
each m is independently 0 to 2, with the proviso that m is 0 or 1 for at least one —C(R 2 ) m —group of each depicted cyclocarbonate group to allow for connection to X.
15. The article of claim 14 , wherein:
X includes 2 or more carbon atoms;
each n is independently 2 or 3; and
each R 2 is independently a hydrogen atom or a carbon-containing group having from 1 to 10 carbon atoms.
16. The article of claim 15 , wherein X includes a cyclic group.
17. The article of claim 3 , wherein one or both of the extender and the polycyclocarbonate compound includes a segment of the below Formula (I):
—Ar—(R t —Ar) t —O— Formula (I)
wherein:
each Ar is independently an aryl group or heteroaryl group;
each t is independently 0 or 1; and
R, if present, is a divalent organic group.
18. The article of claim 17 , wherein each Ar comprises a phenylene group.
19. The article of claim 3 , wherein the food or beverage container, or a portion thereof, includes the coating composition on an interior surface thereof.
20. A coating composition, comprising:
a polyether polymer, wherein the polyether polymer comprises a reaction product of ingredients including: (i) a dihydric monophenol and (ii) a polycyclocarbonate compound; and
a liquid carrier.
21. The coating composition of claim 20 , wherein the polycyclocarbonate compound includes a cyclic group other than a cyclocarbonate group.
22. The coating composition of claim 21 , wherein the cyclic group comprises an aryl or heteroaryl group.
23. The coating composition of claim 21 , wherein the cyclic group comprises an alicyclic group.
24. The coating composition of claim 21 , wherein the cyclic group comprises a polycyclic group.
25. The coating composition of claim 23 , wherein the alicyclic group comprises a cyclobutane group.
26. The coating composition of claim 20 , wherein the polycyclocarbonate compound is a dicyclocarbonate compound, and wherein the two cyclocarbonate groups of the dicyclocarbonate compound each include a 5-member carbonate-containing ring.
27. The coating composition of claim 26 , wherein the polycyclocarbonate compound has a molecular weight of less than 1,000 Daltons.
28. The coating composition of claim 20 , wherein the polycyclocarbonate compound is derived from a diepoxide of a diol containing a cyclic group.
29. The coating composition of claim 20 , wherein the dihydric monophenol comprises substituted or unsubstituted: hydroquinone, resorcinol, catechol, or a combination thereof.
30. The coating composition of claim 20 , wherein the polyether polymer is free of structural units derived from a bisphenol or a diepoxide of a bisphenol.