Glycerol-based epoxy resins

Abstract

An aliphatic epoxy resin precursor composition containing an epoxy component and, optionally, a reactive component, the composition containing no phenols, wherein the epoxy component is a glycerol-based ether, and wherein the precursor composition contains greater than about 60% (w/w) of the epoxy component and between 0% and 30% (w/w) of the reactive component. A cured aliphatic epoxy resin containing a precursor composition and a curing component, the precursor composition including an epoxy component and, optionally, a reactive component, and the cured resin containing no phenols, wherein the epoxy component is a glycerol-based ether, and wherein the precursor composition contains greater than about 60% (w/w) of the epoxy component and between 0% and 30% (w/w) of the reactive component.

1 . An aliphatic epoxy resin precursor composition containing an epoxy component and, optionally, a reactive component, the composition containing no phenols, wherein the epoxy component is a glycerol-based ether, and wherein the precursor composition contains greater than about 60% (w/w) of the epoxy component and between 0% and 30% (w/w) of the reactive component. 
     
     
         2 . A precursor composition according to  claim 1 , wherein the epoxy component is formed by glycidylation of aliphatic alcohols or polyols, and is not derived from phenol or substituted phenol compounds. 
     
     
         3 . A precursor composition according to  claim 1 , wherein the glycerol-based ether is one or more ethers selected from the group including glycerol diglycidyi ether, glycerol triglycidyl ether and diglycerol triglycidyl ether. 
     
     
         4 . A precursor composition according to  claim 1  including the reactive component in an amount between 1% and 30% (w/w), wherein the reactive component is selected from one or more of aliphatic, cycloaliphatic or arylaliphatic diamines, including ethylene diamine, 1,2-propane diamine, 1,3-propane diamine, 2-methyl-1,2-propane diamine, 2,2-dimethyl-1,3-propane diamine, 1,3-butane diamine, 1,4-butane diamine, 1,3-pentane diamine (DAMP), 1,5-pentane diamine, 1,5-diamino-2-methylpentane (MPMD), 2-butyl-2-ethyl-1,5-pentane diamine (C11-Neodiamine), 1,6-hexane diamine, 2,5-dimethyl-1,6-hexane diamine, 2,2,4- and 2,4,4-trimethylhexamethylene diamine (TMD), 1,7-heptane diamine, 1,8-octane diamine, 1,9-nonane diamine, 1,10-decane diamine, 1,1-undecane diamine, 1,12-dodecane diamine, 1,2-, 1,3- and 1,4-diaminocyclohexane, bis-(4-aminocyclohexyl)methane (H, sub, 12-MDA), bis-(4-amino-3-methylcyclohexyl)methane, bis-(4-amino-3-ethylcyclohexyl)methane, bis-(4-amino-3,5-dimethylcyclohexyl)methane, bis-(4-amino-3-ethyl-5-methylcyclohexyl)methane (M-MECA), 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (isophorone diamine or IPD), 2- and 4-methyl-1,3-diaminocyclohexane and mixtures thereof, 1,3- and 1,4-bis- (amino-methyl)cyclohexane, 2,5(2,6)-bis-(aminomethyl)bicyclo[2.2.1 ]heptane (NBDA), 3(4), 8(9)-bis-(aminomethyl)tricyclo[5.2.1.0.sup.2,6]decane, 1,4-diamino-2,2,6-trimethylcyclohexane (TMCDA), 1,8-menthane diamine, 3,9-bis-(3-aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecane as well as 1,3- and 1,4-bis-(aminomethyl)benzene. 
     
     
         5 . A precursor composition according to  claim 4 , wherein the reactive component is 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (isophorone diamine or IPD). 
     
     
         6 . A precursor composition according to  claim 1 , wherein the amount of the epoxy component in the precursor composition is the range of from 60% to 99% (w/w). 
     
     
         7 . A precursor composition according to  claim 1 , wherein the amount of the reactive component in the precursor composition is between 3% and 5% (w/w), or between 1% and 5% (w/w), or between 1% and 3% (w/w), or between 3% and 5% (w/w), or between 3% and 10% (w/w), or about 5% (w/w). 
     
     
         8 . A precursor composition according to  claim 1 , wherein the precursor composition is blended with at least one additive including a cure accelerator, a solvent or diluent, a modifier such as a flow modifier and/or a thickener, a reinforcing agent, a filler, a pigment, a dye, a mold release agent, a wetting agent, a stabilizer, a heat or fire retardant agent, a surfactant, or any combination thereof. 
     
     
         9 . A cured aliphatic epoxy resin containing a curing component and a precursor composition in accordance with  claim 1 . 
     
     
         10 . A cured resin according to  claim 9 , wherein the curing component is one or more of a polyfunctional amine, an acid (or an acid anhydride), a phenol, an alcohol and a thiol. 
     
     
         11 . A cured resin according to  claim 9 , wherein the cured resin contains between about 15% and 40% (w/w) of the reactive component and the curing component combined, or between about 20% and 40% (w/w) of the reactive component and the curing component combined, or between about 20% and 25% (w/w) of the reactive component and the curing component combined. 
     
     
         12 . A cured resin according to  claim 9 , wherein the cured resin includes at least one additive including a cure accelerator, a solvent or diluent, a modifier such as a flow modifier and/or a thickener, a reinforcing agent, a filler, a pigment, a dye, a mold release agent, a wetting agent, a stabilizer, a fire retardant agent, a surfactant, or any combination thereof. 
     
     
         13 . A cured resin according to  claim 12 , wherein the amount of the additives is from about 0% to about 30% (w/w), preferably from about 0.5% to about 5% (w/w), and more preferably from about 0.5% (w/w) to about 3% (w/w), based upon the weight of the cured resin. 
     
     
         14 . A cured aliphatic epoxy resin containing a precursor composition and a curing component, the precursor composition including an epoxy component and, optionally, a reactive component, and the cured resin containing no phenols, wherein the epoxy component is a glycerol-based ether, and wherein the precursor composition contains greater than about 60% (w/w) of the epoxy component and between 0% and 30% (w/w) of the reactive component. 
     
     
         15 . A cured aliphatic epoxy resin containing a precursor composition and a curing component, the precursor composition including an epoxy component and a reactive component, and the cured resin containing no phenols, wherein the epoxy component is a glycerol-based ether, and wherein the precursor composition contains greater than about 60% (w/w) of the epoxy component and between 1% and 30% (w/w) of the reactive component.