Polyester coating compositions containing polymers derived from cyclic carbonates
A coating composition is provided that includes (a) a polyester polymer derived by esterifying an aryloxy ether polyol (e.g., an aryloxy ether diol) derived from reaction between a polyhydric phenol or a polyphenol and a non-hydroxyl functional cyclic carbonate, or from reaction between a monophenol and a hydroxyl functional cyclic carbonate; (b) a crosslinker and (c) an optional catalyst.
1. A coating composition comprising:
(a) a polyester polymer derived by esterifying an aryloxy ether polyol derived from reaction between ingredients including a dihydric phenol and a non-hydroxyl functional cyclic carbonate to provide a diol having Formula III:
wherein:
each R 1 may be the same or different and independently is a monovalent atom or a monovalent organic group and may contain heteroatoms, and wherein at least one R 1 is an organic group having an atomic weight of at least 15 Daltons;
R 2 is hydrogen or an organic group;
x is nearly 0 to about 2; and
y is 1 to about 10;
(b) a crosslinker; and
(c) an optional catalyst.
2. A coating composition according to claim 1 , wherein the aryloxy ether polyol is a diol derived from reaction between a dihydric phenol and a non-hydroxyl functional cyclic carbonate having Formula II:
wherein R 2 is hydrogen or an alkyl group.
3. A coating composition according to claim 1 , wherein the aryloxy ether polyol is derived from a dihydric phenol having an estrogenic agonist activity in an MCF-7 assay less than or equal to that of 4,4′-(1,4-phenylenebis(propane-2,2-diyl)) diphenol.
4. A coating composition according to claim 1 , wherein the cyclic carbonate comprises ethylene carbonate, propylene carbonate, butylene carbonate or glycerine carbonate.
5. A coating composition according to claim 1 , wherein the polyester polymer is derived from ingredients including:
a) maleic acid, fun is acid, succinic acid, adipic acid, phthaiic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, hexahydrophthalic acid, methylhexahydrophthalic acid, endomethylenetetrahydrophthalic acid, azelaic acid, sebacic acid, tetrahydrophthalic acid, isophthalic acid, terephthalic acid, naphthalene dicarboxylic acid, cyclohexane dicarboxylic acid, glutaric acid, a dimer fatty acid, or an anhydride, alkyl ester or mixture thereof, and
b) ethylene glycol, propylene glycol, 1,3-propanediol, 2-methyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, glycerol, diethylene glycol, dipropylene glycol, triethylene glycol, trimethylolpropane, trimethylolethane, tripropylene glycol, neopentyl glycol, pentaerythritol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, 2-methyl-2,4-pentanediol, 4-methyl-2,4-pentanediol, 2,2,4-trimethyl 1-3-pentanediol, 1,5-pentanediol, 1,6-hexanediol, 2,2-dimethyl-1,3-hexanediol, cyclohexanedimethanol, a polyethylene or polypropylene glycol, isopropylidene bis (p-phenylene-oxypropanol-2), hydroxypivalyl hydroxypivalate or mixture thereof.
6. A coating composition according to claim 1 , wherein the polyester polymer is water dispersible or water soluble.
7. A coating composition according to claim 1 , further comprising a carrier liquid comprising an organic solvent, water, or mixture thereof.
8. A coating composition according to claim 1 , wherein the polyester polymer is substantially free of mobile bisphenol A (BPA) and aromatic glycidyl ether compounds.
9. A coating composition according to claim 1 , wherein the coating composition comprises about 10 to about 90 wt. % of the polyester polymer, about 0.1 to about 15 wt. % crosslinker, 0 to about 3 wt. % catalyst and an optional carrier.
10. A food or beverage container article coated on at least one interior surface with a coating composition according to claim 1 .
11. A coating composition according to claim 1 , wherein at least one R 1 comprises a branched hydrocarbon group or an alkenyl group.
12. A coating composition according to claim 1 , wherein at least one R 1 comprises a branched hydrocarbon group.
13. A coating composition according to claim 1 , wherein R 2 is a hydrogen.
14. A coating composition comprising:
(a) a polyester polymer derived by esterifying an aryloxy ether polyol derived from reaction between ingredients including a dihydric phenol and a non-hydroxyl functional cyclic carbonate to provide a diol having Formula III:
wherein:
each R 1 may be the same or different and independently is a monovalent atom or a monovalent organic group and may contain heteroatoms;
R 2 is hydrogen an organic group;
x is nearly 0 to about 2; and
y is to about 10,
wherein the aryloxy ether polyol is derived from catechol, a substituted catechol, a substituted hydroquinone, resorcinol, a substituted resorcinol, or mixture thereof;
(b) crosslinker; and
(c) an optional catalyst.
15. A coating composition comprising:
(a) a polyester polymer derived by esterifying an aryloxy ether polyol derived from reaction between ingredients including a dihydric phenol and a non-hydroxyl functional cyclic carbonate to provide a diol having Formula III:
wherein:
each R 1 may be the same or different and independently is a monovalent atom or a monovalent organic group and may contain heteroatoms;
R 2 is hydrogen or an organic group;
x is nearly 0 to about 2; and
y is 1 to about 10,
wherein the polyester polymer has an acid number less than about 20, a number average molecular weight (Mn) of at least about 1,000 and less than about 20,000, and a Tg of at least 0° C. and less than 100° C.;
(b) a crosslinker; and
(c) an optional catalyst.
16. A coating composition comprising:
(a) a polyester polymer derived by esterifying an aryloxy ether polyol derived from reaction between ingredients including a dihydric phenol and a non-hydroxyl functional cyclic carbonate to provide a diol having Formula III:
wherein:
each R 1 be the same or different and independent is a monovalent atom or a monovalent organic group and may contain heteroatoms;
R 2 is hydrogen or an organic group;
x is nearly 0 to about 2; and
y is 1 to about 10;
(b) crosslinker, wherein the crosslinker comprises a phenolic crosslinker, amino crosslinker, blocked isocyanate crosslinker, material containing oxirane groups, or combination thereof; and
(c) an optional catalyst.
17. A food or beverage container article coated on at least one interior food-contact surface with a coating composition comprising:
(a) a polyester polymer derived by esterifying aryloxy ether polyol derived from reaction between ingredients including a dihydric phenol and a non-hydroxyl functional cyclic carbonate to provide a diol having Formula III:
wherein:
each R 1 may be the same or different and independently is a monovalent atom or a monovalent organic group and may contain heteroatoms;
R 2 is hydrogen or an organic group;
x is nearly 0 to about 2; and
y is 1 to 10;
(b) a crosslinker; and
(c) an optional catalyst.
18. A food or beverage container article coated on at least one interior surface with a coating composition comprising:
(a) a polyester polymer derived by esterifying an aryloxy ether polyol derived from reaction between ingredients including a dihydric phenol and a non-hydroxyl functional cyclic carbonate to provide a diol having Formula III:
wherein:
each R 1 may be the same or different and independent is a monovalent atom or a monovalent organic group and may contain heteroatoms;
R 2 is hydrogen or an organic group;
x is nearly 0 to about 2; and
y is 1 to about 10;
(b) a crosslinker; and
(c) an optional catalyst,
wherein the interior surface comprises a food-contact surface and the article comprises a food or beverage can.