Bisphenol-A replacement materials
View Patent ↗Polymers may include a plurality of tetradecahydroanthracene moieties. Such polymers may be used to make food or beverage containers or medical devices. Food or beverage containers or medical devices may be coated with polymers including a plurality of tetradecahydroanthracene moieties.
1. A coating composition comprising a solvent and a polymer, the polymer comprising at least one repeating unit, wherein the repeating unit comprises a tetradecahydroanthracene moiety represented by Formula I:
wherein:
R 1 -R 4 and R 5 -R 10 are hydrogen and R 9 -R 10 are oxo groups; and
the tetradecahydroanthracene moiety is part of the polymer backbone through the oxo groups.
2. The coating composition of claim 1 , further comprising a drying agent.
3. The coating composition of claim 2 , wherein the drying agent is a metal complex of cobalt, zirconium, zinc, calcium, or iron.
4. The coating composition of claim 2 , wherein the drying agent comprises zirconium octoate, calcium octoate, or cobalt octoate.
5. The coating composition of claim 1 , wherein the solvent is acetone, methyl acetate, ethyl cellosolve, mineral spirits, or water.
6. The coating composition of claim 1 , wherein the polymer further comprises an epoxy, a polyol, an alkyd, a polycarbonate, a polyester, or a polyurethane.
7. The coating composition of claim 1 , wherein the polymer comprises a plurality of tetradecahydroanthracene moieties each represented by Formula II, VI, VII, VIII, IX, or X:
wherein:
R 12 is alkylene, cycloalkylene, or arylene;
R 13 is selected from the group consisting of alkylene, cycloalkylene, or arylene; and
R 14 is independently at each occurrence selected from the group consisting of hydrogen, a polyacrylate, a polyolefin, and a copolymer of an acrylate monomer and a vinyl monomer.
8. The coating composition of claim 1 , wherein the polymer is represented by Formula III, IV, or V:
wherein:
R 11 is independently at each occurrence a fatty acid selected from the group consisting of lauric acid, stearic acid, palmitic acid, oleic acid, linoleic acid, linolenic acid, ricinolenic acid, eleostearic acid, eicosapentaenoic acid, docosahexaenoic acid, stearidonic acid, eicosatrienoic acid, eicosatetraenoic acid, docosapentaenoic acid, clupanodonic acid, tetracosapentaenoic acid, and tetracosahexaenoic acid; and
n is an integer from 1 to 1,000,000.
9. A coating comprising a polymer comprising at least one repeating unit, wherein the repeating unit comprises a tetradecahydroanthracene moiety represented by Formula I:
wherein:
R 1 -R 4 and R 5 -R 10 are hydrogen and R 9 -R 10 are oxo groups; and
the tetradecahydroanthracene moiety is part of the polymer backbone through the oxo groups.
10. The coating of claim 9 , wherein the polymer further comprises an epoxy, a polyol, an alkyd, a polycarbonate, a polyester, or a polyurethane.
11. The coating of claim 9 , wherein the polymer comprises a plurality of tetradecahydroanthracene moieties each represented by Formula II, VI, VII, VIII, IX, or X:
wherein:
R 12 is alkylene, cycloalkylene, or arylene;
R 13 is selected from the group consisting of alkylene, cycloalkylene, or arylene; and
R 14 is independently at each occurrence selected from the group consisting of hydrogen, a polyacrylate, a polyolefin, and a copolymer of an acrylate monomer and a vinyl monomer.
12. The coating of claim 9 , wherein the polymer is represented by Formula III, IV, or V:
wherein:
R 11 is independently at each occurrence a fatty acid selected from the group consisting of lauric acid, stearic acid, palmitic acid, oleic acid, linoleic acid, linolenic acid, ricinolenic acid, eleostearic acid, eicosapentaenoic acid, docosahexaenoic acid, stearidonic acid, eicosatrienoic acid, eicosatetraenoic acid, docosapentaenoic acid, clupanodonic acid, tetracosapentaenoic acid, and tetracosahexaenoic acid; and
n is an integer from 1 to 1,000,000.
13. The coating of claim 9 , wherein the polymer comprises a cross-linked epoxy.
14. The coating of claim 9 , wherein the polymer is an alkyd comprising an esterified polyol backbone comprising a plurality of tetradecahydroanthracene moieties; and a plurality of fatty acid side chains attached to the esterified polyol backbone through ester linkages.
15. The coating of claim 9 , wherein the polymer is a polyurethane which is cross-linked by an diisocyanate agent selected from the group consisting of methylene-bis(4-cyclohexylisocyanate), 2,2-propylene-bis(4-cyclohexylisocyanate), isophorone diisocyanate, hexamethylene diisocyanate, hexamethylene diisocyanate dimer, hexamethylene diisocyanate trimer, polyisocyanates, toluene diisocyanate, methylene-bis(4-phenylisocyanate), benzene diisocyanate, and cyclohexane diisocyanate.
16. A method of coating an article with the coating composition of claim 1 , the method comprising applying the coating composition to the article to form a wet-coated article, and removing the solvent from the coating composition.
17. The method of claim 16 , wherein the applying comprises spray coating the article.
18. The method of claim 16 , wherein the removing comprises allowing the solvent to evaporate, or heating the wet-coated article.
19. The method of claim 16 , wherein the article is a food container, a beverage container, or a medical device.
20. An article comprising the coating of claim 9 .
21. The article of claim 20 which is a food container, a beverage container, or a medical device.