Coating compositions containing reactive diluents and methods
View Patent ↗The present invention provides coating compositions that include reactive diluents and have high performance, low VOC levels, and low irritation levels. Certain embodiments of the present invention include water and water-dispersible polymers and other embodiments do not include water.
1. A method of preparing a coating composition, the method comprising:
providing a mixture comprising a water-dispersible polymer and a reactive diluent,
wherein the water-dispersible polymer is prepared in the presence of the reactive diluent,
wherein the mixture has a viscosity below 100,000 centipoise at processing temperatures, and
further wherein the reactive diluent is present in an amount of 5 wt-% to 40 wt-%, based on the total weight of the reactive diluent and the water-dispersible polymer, and includes a compound having a molecular weight of 350 grams/mole to 1000 grams/mole and, is substantially free of ethylene oxide and propylene oxide moieties and has an OH-functionality of no more than 30 milliequivalents KOH/gram, with the proviso that the reactive diluent does not include pentaerythritol tetraacrylate; and
dispersing the mixture in water.
2. The method of claim 1 wherein the water-dispersible polymer is selected from the group consisting of polyurethanes, epoxies, polyamides, chlorinated polyolefins, acrylics, oil-modified polymers, polyesters, and mixtures or copolymers thereof.
3. The method of claim 2 wherein the water-dispersible polymer is a water-dispersible polyurethane.
4. The method of claim 3 wherein the water-dispersible polyurethane comprises amine or acid functionality.
5. The method of claim 3 wherein the water-dispersible polyurethane comprises ethylenic unsaturation.
6. The method of claim 5 wherein the ethylenic unsaturation comprises (meth)acrylate functionality.
7. The method of claim 5 wherein the ethylenic unsaturation comprises auto-oxidative carbon-carbon double bonds.
8. The method of claim 1 wherein the coating composition further comprises a metal drier.
9. The method of claim 1 wherein the coating composition further comprises a free-radical initiator.
10. The method of claim 1 wherein the coating composition comprises no more than 7 wt-% volatile organic compounds.
11. The method of claim 1 wherein the reactive diluent comprises a compound selected from the group of di-(trimethylolpropane tetraacrylate), di-(trimethylolpropane tetramethacrylate), di-(pentaerythritol hexamethacrylate), dipentaerythritol hexaacrylate, pentaerythritol tetramethacrylate, di-(trimethylolpropane tetravinyl ether), di-(pentaerythritol hexavinyl ether), pentaerythritol tetravinyl ether, di-(trimethylolpropane tetraallyl ether), di-(trimethylolpropane tetramethallyl ether), di(pentaerythritol hexaallyl ether), di-(pentaerythritol hexamethallyl ether), pentaerythritol tetraallyl ether, pentaerythritol tetramethallyl ether, and mixtures thereof.
12. The method of claim 1 wherein the reactive diluent comprises a compound selected from the group consisting of di-(trimethylolpropane tetraacrylate), di-(trimethylolpropane tetramethacrylate), and combinations thereof.
13. The method of claim 1 wherein the reactive diluent comprises a (meth)acrylate, a vinyl ether, a (meth)allyl ether, or mixtures or copolymers thereof.
14. The method of claim 13 wherein the reactive diluent comprises a (meth)acrylate-functional compound.
15. The method of claim 14 wherein the (meth)acrylate-functional compound is selected from the group consisting of di-(trimethylolpropane tetraacrylate), di-(trimethylolpropane tetramethacrylate), and combinations thereof.
16. The method of claim 1 wherein the reactive diluent is present in an amount of 10 wt-% to 30 wt-%, based on the total weight of the reactive diluent and the water-dispersible polymer.
17. The method of claim 1 , wherein the water-dispersible polymer is an oil-modified water-dispersible polymer.
18. The method of claim 17 wherein the oil-modified water-dispersible polymer is an alkyd.
19. The method of claim 17 wherein the oil-modified water-dispersible polymer is an oil-modified water-dispersible polyurethane.
20. The method of claim 19 wherein the reactive diluent is present in an amount of 10 wt-% to 30 wt-%, based on the total weight of the reactive diluent and the oil-modified water-dispersible polymer.
21. The method of claim 19 wherein the reactive diluent comprises a (meth)acrylate, a vinyl ether, a (meth)allyl ether, or mixtures or copolymers thereof.
22. The method of claim 21 wherein the reactive diluent comprises a (meth)acrylate-functional compound.
23. The method of claim 22 wherein the (meth)acrylate-functional compound is selected from the group consisting of di-(trimethylolpropane tetraacrylate), di-(trimethylolpropane tetramethacrylate), and combinations thereof.
24. The method of claim 17 wherein the reactive diluent comprises a compound selected from the group of di-(trimethylolpropane tetraacrylate), di-(trimethylolpropane tetramethacrylate), di-(pentaerythritol hexamethacrylate), pentaerythritol tetramethacrylate, di-(trimethylolpropane tetravinyl ether), di-(pentaerythritol hexavinyl ether), pentaerythritol tetravinyl ether, di-(trimethylolpropane tetraallyl ether), di-(trimethylolpropane tetramethallyl ether), di(pentaerythritol hexaallyl ether), di-(pentaerythritol hexamethallyl ether), pentaerythritol tetraallyl ether, pentaerythritol tetramethallyl ether, and mixtures thereof.
25. The method of claim 24 wherein the oil-modified water-dispersible polymer is an alkyd.
26. The method of claim 24 wherein the mixture comprises no more than 7 wt-% volatile organic compounds.
27. The method of claim 24 wherein the reactive diluent comprises a compound selected from the group consisting of di-(trimethylolpropane tetraacrylate), di-(trimethylolpropane tetramethacrylate), and combinations thereof.
28. The method of claim 24 wherein the mixture further comprises a metal drier.
29. The method of claim 24 wherein the reactive diluent comprises a compound selected from the group of di-(trimethylolpropane tetraacrylate), di-(trimethylolpropane tetramethacrylate), pentaerythritol tetramethacrylate, di-(trimethylolpropane tetravinyl ether), di-(pentaerythritol hexavinyl ether), pentaerythritol tetravinyl ether, di-(trimethylolpropane tetraallyl ether), di-(trimethylolpropane tetramethallyl ether), di(pentaerythritol hexaallyl ether), di-(pentaerythritol hexamethallyl ether), pentaerythritol tetraallyl ether, pentaerythritol tetramethallyl ether, and mixtures thereof.
30. The method of claim 29 wherein the mixture further comprises a metal drier.
31. The method of claim 29 wherein the oil-modified water-dispersible polymer is an alkyd.
32. The method of claim 1 wherein if the reactive diluent is provided as a mixture of compounds, the entire mixture is substantially non-irritating.
33. The method of claim 1 wherein the water-dispersible polymer comprises an acid forming group, and wherein the method further comprises neutralizing the acid forming group with a neutralizing base prior to dispersing the mixture in water.
34. The method of claim 1 wherein the water-dispersible polymer comprises a urethane polymer, and wherein the method further comprises providing chain extenders to the mixture after dispersing the mixture in water.
35. A method of preparing a coating composition, the method comprising:
providing a mixture comprising a water-dispersible polymer and a reactive diluent,
wherein the water-dispersible polymer is prepared in the presence of the reactive diluent,
wherein the mixture has a viscosity below 100,000 centipoise at processing temperatures, and
further wherein the reactive diluent is present in an amount of 5 wt-% to 40 wt-%, based on the total weight of the reactive diluent and the water-dispersible polymer, wherein the reactive diluent is substantially non-irritating; and wherein if the reactive diluent is provided as a mixture of compounds, the entire mixture is substantially non-irritating; and
dispersing the mixture in water.
36. The method of claim 35 wherein the reactive diluent is present in an amount of 10 wt-% to 30 wt-%, based on the total weight of the reactive diluent and the water-dispersible polymer.
37. The method of claim 35 wherein the mixture comprises no more than 7 wt-% volatile organic compounds.
38. The method of claim 35 wherein the water-dispersible polymer comprises a (meth)acrylate-functional water-dispersible polyurethane, and the substantially non-irritating reactive diluent comprises a (meth)acrylate-functional compound.
39. The method of claim 38 wherein the (meth)acrylate-functional compound is selected from the group consisting of di-(trimethylolpropane tetraacrylate), di-(trimethylolpropane tetramethacrylate), and combinations thereof.
40. The method of claim 35 wherein the water-dispersible polymer comprises an oil-modified water-dispersible polyurethane, and the substantially non-irritating reactive diluent comprises a (meth)acrylate-functional compound.
41. The method of claim 40 wherein the (meth)acrylate-functional compound is selected from the group consisting of di-(trimethylolpropane tetraacrylate), di-(trimethylolpropane tetramethacrylate), and combinations thereof.
42. The method of claim 40 wherein the mixture further comprises a metal drier.
43. The method of claim 35 wherein the reactive diluent does not include pentaerythritol tetraacrylate.
44. The method of claim 35 wherein the water-dispersible polymer comprises an acid forming group, and wherein the method further comprises neutralizing the acid forming group with a neutralizing base prior to dispersing the mixture in water.
45. The method of claim 35 wherein the water-dispersible polymer comprises a urethane polymer, and wherein the method further comprises providing chain extenders to the mixture after dispersing the mixture in water.