ACRYLIC RESIN FOR USE IN FLUOROCARBON COATING COMPOSITIONS AND METHOD OF FORMING THE SAME

Abstract

An acrylic resin and method of forming the acrylic resin for use in fluorocarbon coating compositions are disclosed. The fluorocarbon coating composition generally comprises a fluorocarbon resin, a cross-linking agent, and the acrylic resin. The acrylic resin comprises the reaction product of (1) at least one non-functional acrylic monomer, (2) at least one epoxy functional acrylic monomer having an epoxy group, and (3) at least one functional acrylic monomer different than (2). At least one amino compound having a cyclic, heterocyclic, alkyl, or heteroalkyl structure substituted with a primary or secondary amine group is reacted with the epoxy functional acrylic monomer (2) such that the primary or secondary amine opens the epoxy group to obtain the acrylic resin having amine functionality and hydroxyl functionality.

Description

Claims

1. A method of forming an acrylic resin, said method comprising: polymerizing (1) at least one non-functional acrylic monomer and (2) at least one epoxy functional acrylic monomer having an epoxy group; andreacting at least one amino compound having a cyclic, heterocyclic, alkyl, of heteroalkyl structure substituted with a primary or secondary amine group with the epoxy functional acrylic monomer such that the primary or secondary amine opens the epoxy group to obtain the acrylic resin having amine functionality and hydroxyl functionality.

2. A method as set forth in claim 1 wherein the step of reacting the amino compound with the epoxy functional acrylic monomer is further defined as reacting the amino compound with the epoxy functional acrylic monomer after polymerizing (1) and (2)

3. A method as set forth in claim 2 wherein the step of reacting the amino compound occurs within a temperature range of from about 60 to about 140° C.

4. A method as set forth in claim 1 wherein the step of reacting the amino compound with the epoxy functional acrylic monomer is further defined as reacting the amino compound with the epoxy functional acrylic monomer prior to polymerizing (1) and (2).

5. A method as set forth in claim 1 wherein the step of reacting the amino compound occurs within a temperature range of from about 60 to about 140° C.

6. A method as set forth in claim 1 wherein the step of polymerizing (1) and (2) further comprises polymerizing (1) and (2) with (3) at least one functional acrylic monomer different than (2).

7. A method as set forth in claim 6 wherein (3) is selected from at least one of hydroxy ethyl methacrylate, hydroxy propyl methacrylate, hydroxy propyl acrylate, acetoacetoxyethyl methacrylate, and hydroxy ethyl acrylate.

8. A method as set forth in claim 6 wherein the step of reacting the amino compound with the epoxy functional acrylic monomer is further defined as reacting the amino compound with the epoxy functional acrylic monomer after polymerizing (1), (2), and (3).

9. A method as set forth in claim 8 wherein the step of polymerizing (1), (2), and (3) occurs within a temperature range of from about 70 to about 90° C.

10. A method as set forth in claim 1 wherein the amino compound is selected from at least one, of ethyleneurea, pyrrolidine, 2-pyrrolidone, piperidine, morpholine, t-butyl amine, isopropylamine, diisoproylamine, 2-amino-2-methyl-1-propanol, ethanol amine, dicyclohexyl amine, N,N-dimethyl-1,3-propanediamine, dimethyl amine, and diethanol amine.

11. A method as set forth in claim 1 wherein the amino compound is further defined as having a heterocyclic structure.

12. A method as set forth in claim 1 wherein the heterocyclic amino compound is selected from at least one of ethyleneurea, pyrrolidine, 2-pyrrolidone, piperidine, and morpholine.

13. A method as set forth in claim 1 wherein (1) is selected from at least one of methyl methacrylate, ethyl acrylate, ethyl methacrylate, methyl acrylate, butyl acrylate, butyl methacrylate, and tert-butyl methacrylate.

14. A method as set forth in claim 1 wherein (2) is selected from at least one of glycidyl methacrylate, glycidyl acrylate, glycidyl vinyl ether; and glycidyl vinylbenzyl ether.

15. An acrylic resin for use in fluorocarbon coating compositions, said acrylic resin comprising the reaction product of (1) at least one non-functional acrylic monomer;(2) at least one epoxy functional acrylic monomer having an epoxy group; andat least one amino compound having a cyclic, heterocyclic, alkyl, or heteloalkyl structure substituted with a primary or secondary amine group for reacting with said epoxy group and for opening said epoxy group;wherein said acrylic resin has amine functionality from said amino compound to aid in dispersion of fluorocarbon resins in the fluorocarbon coating composition and hydroxyl functionality from opening said epoxy group to enhance cross-linking with cross-linking agents in the fluorocarbon coating composition.

16. An acrylic resin as set forth in claim 15 wherein said acrylic resin further comprises the reaction product of (3) at least one functional acrylic monomer different than (2).

17. An acrylic resin as set forth in claim 16 wherein (3) is selected from at least one of hydroxy ethyl methacrylate, hydroxy propyl methacrylate, hydroxypropyl acrylate, acetoacetoxyethyl methacrylate, and hydroxy ethyl acrylate.

18. An acrylic resin as set forth in claim 15 wherein (1) is selected from at least one of methyl methacrylate, ethyl acrylate, ethyl methacrylate, methyl acrylate, butyl acrylate, butyl methacrylate, and tert-butyl methacrylate.

19. An acrylic resin as set forth in claim 15 wherein (2) is selected from at least one of glycidyl methacrylate, glycidyl acrylate, glycidyl vinyl ether, and glycidyl vinylbenzyl ether.

20. An acrylic resin as set forth in claim 15 wherein said amino compound is selected from at least one of ethyleneurea, pyrrolidine, 2-pyrrolidone, piperidine, and morpholine.

21. An acrylic resin as set forth in claim 16 wherein (1) is present in an amount of about 80 to about 96 percent, (2) is present in an amount of about 0.5 to about 15, and (3) is present in an amount of about 0.1 to about 20 percent, each based on the total weight of said acrylic resin.

22. An acrylic resin as set forth in claim 21 wherein said amino compound is present in an amount of from about 0.1 to about 15 percent based on the total weight of said acrylic resin.

23. A fluorocarbon coating composition comprising: a fluorocarbon resin;a cross-linking agent; andan acrylic resin comprising the reaction product of (1) at least one non-functional acrylic monomer and (2) at least one epoxy functional acrylic monomer having an epoxy group and at least one amino compound having a cyclic, heterocyclic, alkyl, or heteroalkyl structure substituted with a primary or secondary amine group for reacting with said epoxy group and for opening said epoxy group;wherein said acrylic resin has amine functionality from said amino compound to aid in dispersion of said fluorocarbon resin and hydroxyl functionality from opening said epoxy group to enhance cross-linking with said cross-linking agent.

24. A fluorocarbon coating composition as set forth in claim 23 wherein said acrylic resin further comprises the reaction product of (3) at least one functional acrylic monomer different than (2).

25. An acrylic resin as set forth in claim 24 wherein (1) is present in an amount of about 80 to about 95 percent, (2) is present in an amount of about 0.5 to about 15, and (3) is present in an amount of about 0.1 to about 30 percent each based on the total weight of said acrylic resin.

26. An acrylic resin as set forth in claim 25 wherein said amino compound is present in an amount of from about 0.1 to about 15 percent based on the total weight of said acrylic resin.

27. A fluorocarbon coating composition as set forth in claim 24 wherein (3) is selected from at least one of hydroxy ethyl methacrylate, hydroxy propyl methacrylate, hydroxypropyl acrylate, acetoacetoxyethyl methacrylate, and hydroxy ethyl acrylate.

28. A fluorocarbon coating composition as set forth in claim 23 wherein (1) is selected from at least one of methyl methacrylate, ethyl acrylate, ethyl methacrylate, methyl acrylate, butyl acrylate, butyl methacrylate, tert-butyl methacrylate, isopropylamine, diisoproylamine, 2-amino-2-methyl-1-propanol, ethanol amine, dicyclohexyl amine, N,N-dimethyl-1,3-propanediamine, dimethyl amine, and diethanol amine.

29. A fluorocarbon coating composition as set forth in claim 23 wherein (2) is selected from at least one of glycidyl methacrylate, glycidyl acrylate, glycidyl vinyl ether, and glycidyl vinylbenzyl ether.

30. A fluorocarbon coating composition as set forth in claim 23 wherein said amino compound is selected from at least one of ethyleneurea, pyrrolidine, 2-pyrrolidone, piperidine, morpholine, t-butyl amine, isopropylamine, diisoproylamine, 2-amino-2-methyl-1-propanol, ethanol amine, dicyclohexyl amine, N,N-dimethyl-1,3-propanediamine, dimethyl amine, and diethanol amine.

31. A fluorocarbon coating composition as set forth in claim 23 further comprising pigments dispersed in said fluorocarbon resin.

32. A fluorocarbon coating composition as set forth in claim 23 having a solids content of from about 30 to about 70 percent.

33. A fluorocarbon coating composition as set forth in claim 23 wherein said fluorocarbon resin is present in an amount of from about 30 to about 99 percent based on the total weight of the fluorocarbon coating composition.

34. A fluorocarbon coating composition as set forth in claim 23 wherein said acrylic resin is present in an amount of from about 10 to about 60 percent based on the total weight of the fluorocarbon coating composition.

35. A fluorocarbon coating composition as set forth in claim 23 wherein said cross-linking agent is present in an amount of from about 0.2 to about 10 percent based on the total weight of the fluorocarbon coating composition.