Aliphatic polycarbonates for use in thermosetting powder coatings
View Patent ↗A thermosetting polymer material capable of being used in powder coatings. The thermosetting polymer material includes at least one hydroxyl functional aliphatic polycarbonates that is formulated and crosslinked with isocyanates to yield a thermoset organic coating material. These materials provide improved weatherability as compared to prior art powder coating materials while also being less expensive than prior art materials utilizing fluorinated polymers.
1. A composition and a method of forming a coated substrate comprising:
(i) an aliphatic or cycloaliphatic polycarbonate or a combination including at least one of the foregoing polycarbonates, and wherein the polycarbonate has repeating carbonate units of Formula II:
wherein R is a divalent C 1 -C 30 aliphatic radical or a divalent C 3 -C 30 cycloaliphatic radical,
wherein the polycarbonate includes at least one reactive hydroxyl group, said the polycarbonate is derived from a compound of formula I
HO—R—OH Formula I
wherein R is a divalent C 1 -C 30 aliphatic radical or a divalent C 3 -C 30 cycloaliphatic radical;
wherein the polycarbonate has an equivalent molecular weight in a range from 500 grams per mole to 10,000 grams per mole, further wherein the polycarbonate has a T g in a range from 25° C. to 100° C., further wherein the polycarbonate is present in an amount corresponding to from 30 weight percent to 90 weight percent of a total weight of the composition; and
(ii) an isocyanate crosslinking agent having at least one isocyanate functional group, wherein a ratio of isocyanate functional groups to reactive hydroxyl groups of the polycarbonate is in a range of from 0.5:1 to 1.5:1, wherein the composition is a curable powder coating composition.
2. The composition of claim 1 , wherein the composition contains from 0.5 to 5 mol percent of a branching agent selected from tri- and tetra-primary functional alcohols or a combination including at least one of the foregoing compounds.
3. The composition of claim 1 , wherein the compound of formula I is a linear or cyclic aliphatic alcohol selected from neopentyl glycol, hexane diol, hydrogenated bisphenol A, cyclohexanediol, cyclohexane dimethanol, decahydronaphthalene dimethanol, norbornene dimethanol, tetramethylcyclobutanediol, tricyclodecane dimethanol, isosorbide or a combination including at least one of the foregoing compounds.
4. The composition of claim 1 , wherein the compound of formula I includes a combination of tetramethylcyclobutanediol and either neopentyl glycol or cyclohexane dimethanol.
5. The composition of claim 1 , wherein the compound of formula I includes a combination of hydrogenated bisphenol A and either neopentyl glycol or cyclohexane dimethanol.
6. The composition of claim 1 , wherein the compound of formula I includes a combination of tricyclodecanedimethanol and cyclohexane dimethanol, and the hydroxyl equivalent molecular weight of the polycarbonate is from 1,000 to 7,000 and wherein the composition further contains at least one hindered amine light stabilizer that contains 2,2,6,6-tetramethylpiperidine moiety.
7. The composition of claim 1 , wherein the isocyanate crosslinking agent is selected from hexamethylene diisocyanate, isophorone diisocyanate, 4,4′-dicyclohexyl methane diisocyanate, blocked derivatives therefrom, or a combination including at least one of the foregoing isocyanate crosslinking agents.
8. The composition of claim 1 , wherein the Tg of the polycarbonate is in the range of from 50° C. to 80° C.
9. The composition of claim 1 , wherein the equivalent molecular weight of the polycarbonate is in a range from 500 grams per mole to 7,000 grams per mole.
10. The composition of claim 1 , further comprising at least one additive selected from gloss reducing additives, cure catalysts, flow and leveling agents, degassing additives, adhesion promoters, dispersion aids, flame-retardant agents, heat stabilizers, light stabilizers, antioxidants, plasticizers, antistat agents, UV absorbers, lubricants, pigments, dyes, colorants, or combinations including one or more of the foregoing.
11. The composition of claim 10 , wherein at least one of the light stabilizers is a hindered amine light stabilizer that contains 2,2,6,6-tetramethylpiperidine moiety.
12. The composition of claim 11 , wherein at least one of the light stabilizers is selected from bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, 2-[(2-Hydroxyethyl)amino]-4,6-bis[N-(1cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)]butylamino-1,3,5-triazine, or a combination thereof.
13. The composition of claim 1 , wherein the polycarbonate is present in an amount corresponding to from 65 weight percent to 85 weight percent of a total weight of the composition.
14. A cured composition comprising the composition of claim 1 .
15. A substrate coated with the composition of claim 1 .
16. A method of forming a coated substrate comprising:
(a) providing a substrate;
(b) coating the substrate with a curable coating composition to provide a curable coated substrate, wherein the curable coating composition comprises:
(i) an aliphatic or cycloaliphatic polycarbonate or a combination including at least one of the foregoing polycarbonates, and wherein the polycarbonate has repeating carbonate units of Formula II:
wherein R is a divalent C 1 -C 30 aliphatic radical or a divalent C 3 -C 30 cycloaliphatic radical,
wherein the polycarbonate includes at least one reactive hydroxyl group, said the polycarbonate is derived from a compound of formula I
HO—R—OH Formula I
wherein R is a divalent C 1 -C 30 aliphatic radical or a divalent C 3 -C 30 cycloaliphatic radical; wherein the polycarbonate has an equivalent molecular weight in a range from 500 grams per mole to 10,000 grams per mole, further wherein the polycarbonate has a T g in a range from 25° C. to 100° C., further wherein the polycarbonate is present in an amount corresponding to from 30 weight percent to 90 weight percent of a total weight of the composition; and
(ii) an isocyanate crosslinking agent having at least one isocyanate functional group, wherein a ratio of isocyanate functional groups to reactive hydroxyl groups of the polycarbonate is in a range of from 0.5:1 to 1.5:1; and
(c) curing the curable coating composition at a temperature ranging from 100° C. to 250° C.
17. The method of claim 16 , wherein the coating is applied electrostatically using either a spray coating or fluidized bed coating and is then cured under heat to flow and form the resulting coating.
18. The method of claim 16 , wherein the compound of formula I is selected from neopentyl glycol, hexane diol, hydrogenated bisphenol A, cyclohexanediol, cyclohexane dimethanol, decahydronaphthalene dimethanol, norbornene dimethanol, tetramethylcyclobutanediol, tricyclodecane dimethanol, isosorbide or a combination including at least one of the foregoing compounds.
19. The method of claim 16 , wherein the isocyanate crosslinking agent is selected from hexamethylene diisocyanate, isophorone diisocyanate, 4,4′-dicyclohexyl methane diisocyanate, blocked derivatives thereof, or a combination including at least one of the foregoing isocyanate crosslinking agents.
20. The method of claim 16 , wherein the Tg of the polycarbonate is in the range of from 50° C. to 80° C.
21. The method of claim 16 , wherein the equivalent molecular weight of the polycarbonate is in a range from 500 grams per mole to 7,000 grams per mole.
22. The method of claim 16 , wherein the curable coating composition further comprises at least one additive selected from gloss reducing additives, cure catalysts, flame-retardant agents, heat stabilizers, light stabilizers, antioxidants, plasticizers, antistat agents, UV absorbers, lubricants, pigments, dyes, colorants, or combinations including one or more of the foregoing additives.
23. The method of claim 16 , wherein the polycarbonate is present in an amount corresponding to from 65 weight percent to 85 weight percent of a total weight of the composition.
24. An article made by the method of claim 16 .