Epoxy resin compositions and coating systems
Embodiments of the present disclosure generally relate to epoxy resin compositions and coating systems used to form epoxy resin compositions. In an embodiment, an epoxy resin composition is provided. The resin composition includes an epoxy resin; a curing agent; and an acetoacetoxy-functionalized polymer.
1. A resin composition, comprising:
from about 25 wt % to about 99 wt % of a cycloaliphatic epoxy resin;
a curing agent comprising an aliphatic polyamine, a polyetheramine, a cycloaliphatic amine, an aromatic amine, a Mannich base, a ketimine, an oxazoline, an amidoamine, or combinations thereof; and
an acetoacetoxy-functionalized polymer having a weight average molecular weight of about 5,000 g/mol to about 100,000 g/mol, the acetoacetoxy-functionalized polymer comprising:
acetoacetoxy-functionalized monomer units; and
co-monomer units comprising an acrylate monomer, a methacrylate monomer, an alpha-olefin monomer, a vinyl halide monomer, a diester of a carboxylic acid monomer, an unsaturated nitrile monomer, an alpha, beta-unsaturated carboxylic acid monomer, an alpha, beta-unsaturated amide monomer, or combinations thereof.
2. The resin composition of claim 1 , wherein the acetoacetoxy-functionalized polymer comprises:
about 10 wt % to about 30 wt % of the acetoacetoxy-functionalized monomer units; and
about 70 wt % to about 90 wt % of the co-monomer units, a total wt % of the acetoacetoxy-functionalized polymer not to exceed 100 wt %.
3. The resin composition of claim 1 , wherein the acetoacetoxy-functionalized polymer has:
a glass transition temperature of about −50° C. to about 105° C.;
a weight average molecular weight of about 5,000 g/mol to about 60,000 g/mol; or
a combination thereof.
4. The resin composition of claim 1 , wherein:
an amount of the acetoacetoxy-functionalized polymer is from about 1 wt % to about 74 wt % based on a total weight of the resin composition;
an amount of the epoxy resin is from about 25 wt % to about 99 wt % based on the total weight of the resin composition; and
an amount of the curing agent is from about 1 wt % to about 74 wt % based on the total weight of the resin composition, wherein the wt % of each component is based on % solid weight basis, and the total weight of the resin composition does not exceed 100 wt %.
5. The resin composition of claim 1 , wherein the acetoacetoxy-functionalized monomer units, prior to polymerization, comprise an acetoacetoxy-functionalized monomer having the formula (I):
wherein:
R 1 is methyl (CH 3 ) or hydrogen; and
n is a number from 1 to 6.
6. The resin composition from claim 1 , wherein, when the co-monomer units comprise acrylate monomer, methacrylate monomer, or combinations thereof, at least one of the acrylate monomer or the methacrylate monomer, prior to polymerization, comprises a co-monomer having the formula (II):
wherein:
R 2 is methyl or hydrogen; and
R 3 comprises 1 to 30 carbon atoms.
7. The resin composition of claim 6 , wherein:
R 2 is methyl or hydrogen; and
R 3 comprises 1 to 10 carbon atoms.
8. The resin composition of claim 1 , wherein the cycloaliphatic epoxy resin comprises cyclohexane dimethanol diglycidylether, diglycidyl ethers of hydrogenated bisphenol A-type epoxy resins, or combinations thereof.
9. The resin composition of claim 1 , wherein the acetoacetoxy-functionalized polymer comprises a weight average molecular weight of about 10,000 g/mol to about 60,000 g/mol.
10. The resin composition of claim 1 , wherein:
when the curing agent comprises the aliphatic polyamine, the aliphatic polyamine comprises a polyamine of formula (IVa):
wherein n of formula (IVa) is 1, 2, 3, 4, 5, or 6;
when the curing agent comprises the polyetheramine, the polyetheramine amine comprises a polyetheramine of formula (IVb), a polyetheramine of formula (IVc), a polyetheramine of formula (IVd), a polyetheramine of formula (IVe), or combinations thereof:
wherein x of formula (IVb) is from 2.5 to 68;
wherein x+y+z of formula (IVc) is from 5 to 85;
wherein R 4 of formula (IVd) is hydrogen or CH 3 , x of formula (IVd) is from 1 to 40, and y of formula (IVd) is from 1 to 40; or
wherein x+z of formula (IVe) is from 1.2 to 6 and y of formula (IVe) is from 2 to 39; or
combinations thereof.
11. The resin composition of claim 1 , wherein the curing agent is selected from the group consisting of 1,3-bis(aminomethyl)cyclohexane, diethylenetriamine, hexamethylenediamine, trimethylhexamethylenediamine, triethylenetetramine, tetraethylenepentaamine, N,N′,-dimethylpropylenediamine, 1,3-bis(4-amino-3-methylcyclohexyl)methane, bis(p-aminocyclohexyl)methane, 2,2-bis(4-aminocyclohexyl)propane, 3,5,5-trimethyl-3-(aminomethyl)-cyclohexylamine, N-aminoethlpiperazine, m-phenylenediamine, p-phenylenediamine, bis(p-aminophenyl)methane, bis(p-aminophenyl)sulfone, m-xylylenediamine, 1,2-diaminocyclohexane, 1,4-diaminocyclohexane, 1,4-bis(aminomethyl)cyclohexane, and combinations thereof.
12. The resin composition of claim 1 , further comprising about 0.1 wt % to about 50 wt % of a solvent based on a total weight of the resin composition.
13. A composition comprising an epoxy polymerization product of a reaction mixture, the reaction mixture comprising:
from about 25 wt % to about 99 wt % of a cycloaliphatic epoxy resin;
a curing agent comprising an aliphatic polyamine, a polyetheramine, a cycloaliphatic amine, an aromatic amine, a Mannich base, a ketimine, an oxazoline, an amidoamine, or combinations thereof; and
an acetoacetoxy-functionalized polymer having a weight average molecular weight of about 5,000 g/mol to about 100,000 g/mol, the acetoacetoxy-functionalized polymer comprising:
acetoacetoxy-functionalized monomer units; and
co-monomer units comprising an acrylate monomer monomer, a methacrylate monomer, an alpha-olefin monomer, a vinyl halide monomer, a diester of a carboxylic acid monomer, an unsaturated nitrile monomer, an alpha, beta-unsaturated carboxylic acid monomer, an alpha, beta-unsaturated amide monomer, or combinations thereof.
14. The composition of claim 13 , wherein the acetoacetoxy-functionalized polymer comprises:
about 10 wt % to about 30 wt % of the acetoacetoxy-functionalized monomer units; and
about 70 wt % to about 90 wt % of the co-monomer units, a total wt % of the acetoacetoxy-functionalized polymer not to exceed 100 wt %.
15. The composition of claim 13 , wherein the acetoacetoxy-functionalized polymer has:
a glass transition temperature of about −50° C. to about 105° C.;
a weight average molecular weight of about 5,000 g/mol to about 60,000 g/mol; or
a combination thereof.
16. The composition of claim 13 , wherein:
an amount of the acetoacetoxy-functionalized polymer is from about 1 wt % to about 74 wt % based on a total weight of the composition;
an amount of the epoxy resin is from about 25 wt % to about 99 wt % based on the total weight of the composition; and
an amount of the curing agent is from about 1 wt % to about 74 wt % based on the total weight of the composition, wherein the wt % of each component is based on % solid weight basis, and the total weight of the composition does not exceed 100 wt %.
17. The composition of claim 13 , wherein:
the acetoacetoxy-functionalized monomer units, prior to polymerization, comprise an acetoacetoxy-functionalized monomer having the formula (I):
wherein:
R 1 is methyl (CH 3 ) or hydrogen; and
n is a number from 1 to 6;
when the co-monomer units comprise acrylate monomer, methacrylate monomer, or combinations thereof, at least one of the acrylate monomer or the methacrylate monomer, prior to polymerization, comprises a co-monomer having the formula (II):
wherein:
R 2 is methyl or hydrogen; and
R 3 comprises 1 to 30 carbon atoms; or
a combination thereof.
18. A coating system, comprising:
a first component, comprising:
from about 25 wt % to about 99 wt % of the coating system of a cycloaliphatic epoxy resin; and
an acetoacetoxy-functionalized polymer having a molecular weight of about 5,000 g/mol to about 100,000 g/mol, the acetoacetoxy-functionalized polymer comprising:
acetoacetoxy-functionalized monomer units; and
co-monomer units comprising an acrylate monomer, a methacrylate, an alpha-olefin, a vinyl halide monomer, a diester of a carboxylic acid monomer, an unsaturated nitrile monomer, an alpha, beta-unsaturated carboxylic acid monomer, an alpha, beta-unsaturated amide monomer, or combinations thereof; and
a second component comprising a curing agent comprising an aliphatic polyamine, a polyetheramine, a cycloaliphatic amine, an aromatic amine, a Mannich base, a ketimine, an oxazoline, an amidoamine, or combinations thereof.
19. The coating system of claim 18 , wherein:
the acetoacetoxy-functionalized polymer comprises about 10 wt % to about 30 wt % of the acetoacetoxy-functionalized monomer units;
the acetoacetoxy-functionalized polymer has a glass transition temperature of about −50° C. to about 105° C.;
the acetoacetoxy-functionalized polymer has a weight average molecular weight of about 5,000 g/mol to about 60,000 g/mol; or
combinations thereof.