Binder compositions and methods for making and using same

Abstract

Binder compositions and methods for making and using same are provided. In at least one specific embodiment, the binder composition can include at least one unsaturated compound having two or more unsaturated carbon-carbon bonds and at least one free radical precursor. At least one of the unsaturated carbon-carbon bonds can be a pi-bond that is not conjugated with an aromatic moiety and can be capable of free radical addition. The free radical precursor can be present in an amount of about 7 wt % to about 99 wt %, based on the weight of the one or more unsaturated compounds.

What is claimed is: 
     
         1 . A binder composition, comprising:
 an unsaturated compound comprising a reaction product of an unsaturated epoxide and an unsaturated polyester prepolymer, wherein the unsaturated polyester prepolymer comprises a reaction product of a polyol and an acid anhydride, wherein:
 the unsaturated epoxide comprises allyl glycidyl ether, 3,4-epoxy-1-butene, 1,2-epoxy-5-hexene, or a mixture thereof, 
 the polyol comprises ethylene glycol, diethylene glycol, triethylene glycol, glycerol, polyglycerol, pentaerythritol, trimethylolpropane, diethanolamine, triethanolamine, ethyl diethanolamine, methyl diethanolamine, sorbitol, glucose, fructose, sucrose, starch, dextrin, maltodextrin, polyvinyl alcohol, hydroxyethylcellulose, 1,4-cyclohexanediol, 2-butene-1,4-diol, hydroxyl-terminated polybutadiene, or a mixture thereof, and 
 the acid anhydride comprises phthalic anhydride, mellitic anhydride, pyromellitic anhydride, maleic anhydride, or a mixture thereof; and 
   a free radical precursor comprising an oxidant and a catalyst.   
     
     
         2 . The binder composition of  claim 1 , wherein the oxidant comprises hydrogen peroxide, an alkali metal salt of percarbonate, an alkali metal salt of perborate, an alkali metal salt of peroxysulfate, an alkali metal salt of peroxyphosphate, an alkali metal salt of peroxysilicate, t-butyl peroxide, benzoyl peroxide, peroxy carboxylic acids, peracetic acid, perbenzoic acid, t-butyl hydroperoxide, an alkali metal chlorite, an alkali metal hypochlorite, chlorine dioxide, a chloro sodium salt of cyanuric acid, dimethyloxirane, or a mixture thereof. 
     
     
         3 . The binder composition of  claim 1 , wherein the oxidant comprises an inorganic oxidant. 
     
     
         4 . The binder composition of  claim 1 , wherein a weight ratio of the free radical precursor to the unsaturated compound is about 0.05:1 to about 40:1. 
     
     
         5 . The binder composition of  claim 1 , wherein the catalyst comprises an iron containing catalyst comprising potassium ferricyanide, iron (II) sulfate, iron (III) sulfate, an iron complex of ethylenediamine tetraacetic acid, an iron complex of ethylenediamine-N,N′-disuccinic acid, an iron complex of diethylenetriamine pentaacetic acid, an iron complex of ethyleneglycol bis(2-aminoethylether)-N,N,N′,N′-tetraacetic acid, an iron complex of trans-1,2-diaminocyclohexanetetraacetic acid, or a mixture thereof. 
     
     
         6 . The binder composition of  claim 1 , wherein a weight ratio of the free radical precursor to the unsaturated compound is at least 0.23:1 to about 40:1. 
     
     
         7 . The binder composition of  claim 6 , wherein the oxidant comprises hydrogen peroxide and the catalyst comprises an iron containing catalyst. 
     
     
         8 . The binder composition of  claim 1 , wherein:
 the unsaturated epoxide comprises allyl glycidyl ether,   the polyol comprises polyglycerol,   the acid anhydride comprises maleic anhydride,   the oxidant comprises hydrogen peroxide, and   the catalyst comprises an iron containing catalyst.   
     
     
         9 . The binder composition of  claim 1 , wherein:
 the unsaturated epoxide comprises allyl glycidyl ether,   the polyol comprises pentaerythritol,   the acid anhydride comprises maleic anhydride,   the oxidant comprises hydrogen peroxide, and   the catalyst comprises an iron containing catalyst.   
     
     
         10 . The binder composition of  claim 1 , wherein:
 the unsaturated epoxide comprises allyl glycidyl ether,   the polyol comprises sorbitol,   the acid anhydride comprises maleic anhydride,   the oxidant comprises hydrogen peroxide, and   the catalyst comprises an iron containing catalyst.   
     
     
         11 . The binder composition of  claim 1 , further comprising a second unsaturated compound comprising dicyclopentadiene, ethylene glycol diacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, poly(ethylene glycol) diacrylate, poly(ethylene glycol) dimethacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, polyacrylate starch, or a mixture thereof. 
     
     
         12 . A process for making a binder composition, comprising:
 reacting a polyol and an acid anhydride to produce an unsaturated polyester prepolymer, wherein:
 the polyol comprises ethylene glycol, diethylene glycol, triethylene glycol, glycerol, polyglycerol, pentaerythritol, trimethylolpropane, diethanolamine, triethanolamine, ethyl diethanolamine, methyl diethanolamine, sorbitol, glucose, fructose, sucrose, starch, dextrin, maltodextrin, polyvinyl alcohol, hydroxyethylcellulose, 1,4-cyclohexanediol, 2-butene-1,4-diol, hydroxyl-terminated polybutadiene, or a mixture thereof, and 
 the acid anhydride comprises phthalic anhydride, mellitic anhydride, pyromellitic anhydride, maleic anhydride, or a mixture thereof; 
   reacting the unsaturated polyester prepolymer and an unsaturated epoxide to produce an unsaturated compound, wherein the unsaturated epoxide comprises allyl glycidyl ether, 3,4-epoxy-1-butene, 1,2-epoxy-5-hexene, or a mixture thereof; and   mixing the unsaturated compound with a free radical precursor comprising an oxidant and a catalyst to produce the binder composition.   
     
     
         13 . The process of  claim 12 , wherein:
 the unsaturated epoxide comprises allyl glycidyl ether,   the polyol comprises polyglycerol, pentaerythritol, sorbitol, or a mixture thereof,   the acid anhydride comprises maleic anhydride,   the oxidant comprises hydrogen peroxide, and   the catalyst comprises an iron containing catalyst.   
     
     
         14 . The process of  claim 13 , wherein a weight ratio of the free radical precursor to the unsaturated compound is at least 0.23:1 to about 40:1, and wherein the oxidant comprises hydrogen peroxide and the catalyst comprises an iron containing catalyst. 
     
     
         15 . The process of  claim 14 , wherein the iron containing catalyst comprises potassium ferricyanide, iron (II) sulfate, iron (III) sulfate, an iron complex of ethylenediamine tetraacetic acid, an iron complex of ethylenediamine-N,N′-disuccinic acid, an iron complex of diethylenetriamine pentaacetic acid, an iron complex of ethyleneglycol bis(2-aminoethylether)-N,N,N′,N′-tetraacetic acid, an iron complex of trans-1,2-diaminocyclohexanetetraacetic acid, or a mixture thereof. 
     
     
         16 . A process for making a composite product, comprising:
 combining a plurality of lignocellulose substrates, an unsaturated compound, and a free radical precursor to produce a resinated furnish, wherein:
 the unsaturated compound comprises a reaction product of an unsaturated epoxide and an unsaturated polyester prepolymer, wherein the unsaturated polyester prepolymer comprises a reaction product of a polyol and an acid anhydride, wherein:
 the unsaturated epoxide comprises allyl glycidyl ether, 3,4-epoxy-1-butene, 1,2-epoxy-5-hexene, or a mixture thereof, 
 the polyol comprises ethylene glycol, diethylene glycol, triethylene glycol, glycerol, polyglycerol, pentaerythritol, trimethylolpropane, diethanolamine, triethanolamine, ethyl diethanolamine, methyl diethanolamine, sorbitol, glucose, fructose, sucrose, starch, dextrin, maltodextrin, polyvinyl alcohol, hydroxyethylcellulose, 1,4-cyclohexanediol, 2-butene-1,4-diol, hydroxyl-terminated polybutadiene, or a mixture thereof, and 
 the acid anhydride comprises phthalic anhydride, mellitic anhydride, pyromellitic anhydride, maleic anhydride, or a mixture thereof; and 
 
 the free radical precursor comprises an oxidant and a catalyst; and 
   heating the resinated furnish to a temperature of about 60° C. to about 300° C. to produce the composite product.   
     
     
         17 . The process of  claim 16 , wherein the resinated furnish is compressed in a press under a pressure of about 0.5 MPa to about 11 MPa when the resinated furnish is heated. 
     
     
         18 . The process of  claim 17 , wherein the press is a closed press. 
     
     
         19 . The process of  claim 17 , wherein the press is an open press. 
     
     
         20 . The process of  claim 17 , wherein the composite product comprises particleboard, fiberboard, plywood, oriented strand board, parallel strand lumber, or laminated veneer lumber.