Renewable Bio-Based (Meth)Acrylated Monomers as Vinyl Ester Cross-Linkers

Abstract

Anhydrosugar-based monomers prepared from isosorbide, isomannide, and isoidide and resin systems containing these anhydrosugar-based monomers that are partially to fully bio-based, which may produce materials having properties that meet or exceed the properties of similar petroleum derived vinyl ester resins.

1 . A polymerizable monomer selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         2 . A polymerizable monomer as claimed in  claim 1 , wherein the monomer is: 
       
         
           
           
               
               
           
         
       
     
     
         3 . (canceled) 
     
     
         4 . A polymerizable monomer as claimed in  claim 1 , wherein the monomer is: 
       
         
           
           
               
               
           
         
       
     
     
         5 - 13 . (canceled) 
     
     
         14 . A method of making a polymer comprising the step of curing a composition comprising at least one monomer selected from the group consisting of 
       
         
           
           
               
               
           
         
       
     
     
         15 . The method of  claim 14 , wherein the curing is carried out by free-radical curing. 
     
     
         16 . The method of  claim 14 , wherein the composition further comprises from 1 to 99% by weight of at least one reactive diluent. selected from the group consisting of: styrene, 2-hydroxymethacrylate, methyl methacrylate, methyl acrylate, furfuryl methacrylate, methacyrlated lauric acid methacrylated fatty acids. 
     
     
         17 . The method of  claim 16 , wherein the reactive diluent is selected from the group consisting of: styrene, 2-hydroxymethacrylate, methyl methacrylate, methyl acrylate, furfuryl methacrylate, methacyrlated lauric acid methacrylated fatty acids. 
     
     
         18 . The method of  claim 14 , wherein the composition further comprises from 1 to 99% by weight of at least one cross-linking agent. 
     
     
         19 . The method of  claim 18 , wherein the crosslinker is selected from the group consisting of: unsaturated polyester, vinyl ester and the structures in  claim 1 . 
     
     
         20 . The method of  claim 27 , wherein said composition comprises 50-95% by weight of said at least one monomer and 5-50% by weight of said reactive diluent 
     
     
         21 . A polymer obtained by the process of  claim 14 . 
     
     
         22 . A method of making a polymer comprising the step of curing a composition comprising at least one anhydrosugar-based monomer selected from the group consisting of 
       
         
           
           
               
               
           
         
       
       and at least one vinyl ester resin monomer or unsaturated polyester monomer. 
     
     
         23 . The method of  claim 22 , wherein the composition comprises 1-99% by weight of anhydrosugar-based monomers, 1-70% by weight of vinyl ester resin monomer and/or unsaturated polyester monomer and 0-60% by weight of at least one reactive diluent. 
     
     
         24 . The method of  claim 22  wherein the composition comprises 5-95% by weight by weight of anhydrosugar-based monomers, 5-65% by weight of vinyl ester resin monomer and/or unsaturated polyester monomer and 0-50% by weight of at least one reactive diluent. 
     
     
         25 . The method of  claim 22 , wherein the composition comprises 15-90% by weight of anhydrosugar-based monomers, 10-55% by weight of vinyl ester resin monomer and/or unsaturated polyester monomer and 0-45% by weight of at least one reactive diluent. 
     
     
         26 . The method of  claim 23 , wherein the reactive diluent is selected from the group consisting of: styrene, 2-hydroxymethacrylate, methyl methacrylate, methyl acrylate, furfuryl methacrylate, methacyrlated lauric acid and methacrylated fatty acids. 
     
     
         27 . The method of  claim 26 , wherein the vinyl ester monomer is selected from the group consisting of (meth)acrylated glycidyl ethers of bisphenols, (meth)acrylated ethoxylated bisphenols and novolac vinyl esters. 
     
     
         28 . The method of  claim 27 , wherein the bisphenols are selected from the group consisting of: bisphenol A, hexafluorobisphenol A, bisphenol E, bisphenol F, tetramethyl bisphenol E, tetramethyl bisphenol F, bisphenol M, bisphenol C, bisphenol P and bisphenol Z. 
     
     
         29 . The method of  claim 28 , wherein the unsaturated polyester monomer is made from one or more of the following components: phthalic acid, terephtalic acid, m-phthalic acid, suberic acid, adipic acid, succinic acid, maleic acid, fumaric acid, butylene glycol, propylene glycol, and ethylene glycol. 
     
     
         30 . A polymer obtained by the method of  claim 23 .