High throughput process for reactive extrusion of epoxy resin

Abstract

The present invention provides low cost resins (e.g., advanced epoxy resins), processes for making these resins, and coatings made with theses resins. Specifically, the present invention provides high throughput extrusion processing of advanced epoxy resins using an appropriate amount of an iminium salt catalyst. Preferred iminium salt catalysts are stable at room temperature in the reaction mixture (thereby enabling the pre-mixing of ingredients and the stable storage of the pre-mixed ingredients) and yet are highly efficient at the processing temperatures described herein. An example of one such advance epoxy resin is the reaction product of diglycidyl ether of bisphenol A with bisphenol A in the presence of an iminium salt catalyst. Preferred processes are performed using no solvent or only negligible amounts of solvent. One preferred extrusion process utilizes an intermeshing co-rotating twin-screw extruder, however, other types of extruders may alternatively be employed.

1 .- 18 . (Cancelled)  
     
     
         19 . An advanced epoxy resin formed by an extrusion process, wherein the advanced epoxy resin is the extruded reaction product of an epoxy resin and a linking material in the presence of an iminium salt catalyst.  
     
     
         20 . The advanced epoxy resin of  claim 19 , wherein the advanced epoxy resin further comprises a curing agent.  
     
     
         21 . An advanced epoxy resin composition, comprising: 
 a polyepoxide;    an iminium salt compound having the formula      [R1R2R3P=M+=PR4R5R6]X−,    wherein M is Nitrogen or Phosphorus, and wherein each of R1, R2, R3, R4, R5, and R6 is independently an aromatic, inertly substituted aromatic, aliphatic, cycloaliphatic, inertly substituted aliphatic, or inertly substituted cycloaliphatic group, and wherein X is any suitable anion; and    a curing agent.    
     
     
         22 . The composition of  claim 21 , wherein at least one of R1, R2, and R3 is an aromatic group, and at least one of R4, R5, and R6 is an aromatic group.  
     
     
         23 . The composition of  claim 21 , wherein the imimium salt compound is a bis(trihydrocarbylphosphine)iminium salt, bis(triphenylphosphine)iminium salt, bis[tris(dihydrocarbylamino)phosphine]iminium salt, tetrakis[tris(dihydrocarbylamino)phosphoranylideneamino]phosphonium salt, or combinations thereof  
     
     
         24 . The composition of  claim 21 , wherein the suitable anion is a halide, carboxylate, carboxylic acid complex, phosphate, borate, conjugate base of an inorganic acid, conjugate base of a phenol, an anion derived from a bisphenol or biphenol, or combinations thereof.  
     
     
         25 . The composition of  claim 21 , wherein the iminium salt compound is present from about 0.01% to about 3% by weight of the total composition.  
     
     
         26 . The composition of  claim 21 , wherein the curing agent is a phenol-aldehyde resole resin, a urea-aldehyde resin, a melamine-aldehyde resin, a polyamide, an acid anhydride, a primary, secondary or tertiary amine, an imidazole, a guanadine, or combinations thereof.  
     
     
         27 . The composition of  claim 21 , wherein the curing agent is present from about 1 to about 30 moles of curing agent per epoxide group.  
     
     
         28 . The composition of  claim 21 , wherein the curing agent is present from about 10 to about 25 moles of curing agent per epoxide group.  
     
     
         29 . The composition of  claim 21 , further comprising a chain terminator.  
     
     
         30 . The composition of  claim 30 , wherein the chain terminator is a monofunctional phenolic compound, carboxylic acid, aromatic or aliphatic secondary amine, mercaptan, isocyanate, isothiocyanate, epoxy compound, or combinations thereof.  
     
     
         31 . The composition of  claim 31 , wherein the chain terminator is phenol, p-tertiary butyl phenol, nonyl phenol, stearic acid, talloil acid, octyl mercaptan, dodecyl mercaptan, butyl glycidyl ether, octyl glycidyl ether, phenyl isocyanate, or combinations thereof.  
     
     
         32 . The composition of  claim 21 , further comprising an antioxidant.  
     
     
         33 . The composition of  claim 21 , further comprising a pigment or dye.  
     
     
         34 . The composition of  claim 21 , further comprising a filler.  
     
     
         35 . The composition of  claim 21 , further comprising a flow control agent.  
     
     
         36 . The composition of  claim 21 , further comprising a leveling agent.  
     
     
         37 . The composition of  claim 21 , wherein the composition has an average weight average molecular weight from about 400 to about 200,000.  
     
     
         38 . The composition of  claim 21 , wherein the composition has an average weight average molecular weight from about 5,000 to about 90,000.