Curable Bicyclic Compound Derived from Biomass, Solvent-Free Curable Composition, and Method for Preparing Same

Abstract

The present invention relates to a curable bicyclic compound derived from biomass, solvent-free curable composition and a method for preparing thereof. The curable compound derived from biomass according to the invention comprises a bicycle structure, to which one of two epoxide functional groups are bonded.

1 . A curable bicyclic compound derived from biomass, having any one of the following chemical structures from I to V, comprising a bicycle structure as a basic backbone, to which one or two epoxide functional groups, 
       
         
           
           
               
               
           
         
       
     
     
         2 . A solvent-free curable composition comprising the curable bicyclic compound according to  claim 1 , and an initiator or curing agent. 
     
     
         3 . The solvent-free curable composition according to  claim 2 , wherein the initiator is a cationic curing initiator. 
     
     
         4 . A method for preparing a curable bicyclic compound derived from biomass, the method comprising:
 a step of preparing a starting material wherein furan and maleic anhydride are prepared as a starting material, using respectively hemicellulose and cellulose extracted from carbohydrate-based biomass;   a step of reacting intermediately the maleic anhydride and the furan derived from biomass through Diels-Alder reaction and consecutive reduction to form an intermediate compound comprising bicycle and two alcohol functional groups; and   a step of reacting finally the intermediate compound and an epichlorohydrin to produce a compound comprising bicycle and two epoxide functional groups.   
     
     
         5 . The method for preparing a curable bicyclic compound derived from biomass according to  claim 4 ,
 wherein the step of reacting intermediately further comprises a step of reducing by hydrogenation wherein a second intermediate compound is prepared by hydrogenating reduction of the intermediate compound formed, and the step of reacting finally is to react the second intermediate compound and the epichlorohydrin.   
     
     
         6 . A method for preparing a curable bicyclic compound derived from biomass, the method comprising:
 a step of preparing a starting material wherein furan is prepared as a starting material, using hemicellulose extracted from carbohydrate-based biomass;   a step of reacting intermediately the furan and methyl acrylate through Diels-Alder reaction and reduction to form an intermediate compound comprising an alcohol functional group and bicycle; and   a step of reacting finally the intermediate compound and an epichlorohydrin to produce a compound comprising an epoxide functional group and bicycle.   
     
     
         7 . The method for preparing a curable bicyclic compound derived from biomass according to  claim 6 ,
 wherein the step of reacting intermediately separates the compounds formed after the Diels-Alder reaction into endo type and exo type compounds respectively, and then conducts reducing the separated compounds respectively.   
     
     
         8 . The method for preparing a curable bicyclic compound derived from biomass according to  claim 6 ,
 wherein the step of reacting intermediately further comprises a step of reducing by hydrogenation wherein a second intermediate compound is formed by hydrogenating reduction of the intermediate compound formed, and the step of reacting finally is to react the second intermediate compound and the epichlorohydrin.   
     
     
         9 . The method for preparing a curable bicyclic compound derived from biomass according to  claim 4 ,
 wherein the step of reacting finally is to react a mixture comprising the intermediate compound or the second intermediate compound and the epichlorohydrin using PTC (Phase Transfer Catalyst) as a catalyst in a bi-phasic solvent system where a sodium hydroxide aqueous solution is added.   
     
     
         10 . The method for preparing a solvent-free composition comprising a step of preparing a composition wherein a curable adhesive composition is prepared by mixing the curable bicyclic compound derived from biomass prepared according to  claim 4 , and cationic curing initiator or curing agent.