Furan based resin, process for the preparation thereof, and use of the compound

Abstract

The present invention relates to the polymeric reaction product of compounds according to Formula (I) and Formula (II) or (III). Formula (I) has the following structure: where R 1 , R 2 , R 3 and R 4 are independently H, OH, optionally substituted C 1-12 alkyl, optionally substituted C 1-12 alkenyl, C 1-12 aldehyde, C 3-12 acetals, C 2-12 ether, and/or C 2-12 ester; where optionally at least one of R 1 , R 2 , R 3 and R 4 is H. Formulae (II) and (III) have the following structure: where X is H or C 1-4 alkyl; Y is OH or OR 5 where R 5 is C 1-12 alkyl, C 3-12 aryl, C 4-12 aralkyl or C 3-12 cycloalkyl; and Z is an electron-withdrawing group.

1 . A polymeric reaction product of a compound according to formula (I): 
       
         
           
           
               
               
           
         
       
       where:
 R 1 , R 2 , R 3  and R 4  are independently selected from the group consisting of H, OH and optionally substituted C 1-18 hydrocarbo (optionally further substituted by at least one substituent selected from the group consisting of oxy and carbonyl), where optionally at least one of R 1 , R 2 , R 3  and R 4  is H; and 
 at least one compound according to formula (II) or (III): 
 
       
         
           
           
               
               
           
         
       
       where:
 X is selected from the group consisting of H and C 1-6 hydrocarbo; 
 Y is selected from the group consisting of OH and OR 5  where R 5  is C 1-18 hydrocarbo; and 
 Z is an electron-withdrawing group which draws electrons away from the atom to which Z is attached. 
 
     
     
         2 . The polymer according to  claim 1 , in which:
 in formula (I) R 1 , R 2 , R 3  and R 4  are independently H, OH, substituted or unsubstituted C 1-12 alkyl, substituted or unsubstituted C 1-12 alkenyl, C 1-12 aldehyde, C 3-12 acetals, C 2-12  ether, or C 2-12  ester; where at least one of R 1 , R 2 , R 3  and R 4  is H; and   in formula (II) and/or (III), X is H or C 1-4  alkyl; Y is OH or OR 5  where R 5  is C 1-12 alkyl, C 3-12 aryl, C 4-12 aralkyl or C 3-12 cycloalkyl; and Z is an acid- (e.g. carboxy), ester (e.g. carbonyloxy), carbonyl, cyano, di-alkylacetal, aldehyde, substituted phenyl, trihalomethyl and/or halo group.   
     
     
         3 . The product according to  claim 1 , where R 1 , R 2 , R 3  and R 4  are independently H, C 1-6 alkyl, C 1-6 alkenyl, carboxy substituted C 1-5 alkyl, carboxy substituted C 1-5 alkenyl, hydroxy substituted C 1-6 alkyl, or hydroxy substituted C 1-6 alkenyl. 
     
     
         4 . The product according to  claim 1 , where R 1 , R 2 , R 3  and R 4  are independently H, —CH 3 , —CH 2 OH, —CH═O, or —COOH. 
     
     
         5 . The product according to  claim 1 , wherein the compound of formula (I) is selected from the group consisting of: furan, furfural, furfuryl alcohol, hydroxy methyl furan, bis-hydroxy methyl furan, furan dicarboxylic acid, furan carboxylic acid, hydroxymethyl furfunal, hydroxymethyl furan carboxylic acid, combinations thereof and mixtures thereof. 
     
     
         6 . The product according to  claim 1  wherein the compound of formula (II) is selected from the group consisting of: glyoxylic acid, pyruvic acid, methylglyoxylate, ethylglyoxylate, methyl pyruvate, ethyl pyruvate, methylglyoxylate methanol hemiacetal, ethylglyoxylate ethanol hemiacetal, ethylglyoxylate methanol hemiacetal, butylglyoxylate butanol hemiacetal, butylglyoxylate methanol hemiacetal, butylglyoxylate ethanol hemiacetal, isopropylglyoxylate isopropanol hemiacetal, propylglyoxylate propanol hemiacetal, cyclohexylglyoxylate methanol hemiacetal, 2-ethylhexylglyoxylate methanol hemiacetal, combinations thereof and mixtures thereof. 
     
     
         7 . A resin produced from the reaction product according to  claim 1 . 
     
     
         8 . A resin comprising the following polymeric structure: 
       
         
           
           
               
               
           
         
       
       where:
 R 8  and R 9  are independently H, OH, substituted or unsubstituted C 1-12 alkyl, substituted or unsubstituted C 1-12 aldehyde, C 1-12 acetal, C 3-12 acetal, C 2-12 ether, or C 2-12 ester; 
 R 7  and R 10  are independently nil, —O—, substituted or unsubstituted C 1-12 alkyl, substituted or unsubstituted C 1-12 alkenyl, C 1-12 aldehyde, C 3-12 acetal, C 2-12 ether, or C 2-12 ester; 
 X is H or C 1-4 alkyl; 
 Z is an electron-withdrawing group. 
 
     
     
         9 . An article comprising a resin according to  claim 7 . 
     
     
         10 . Use of a resin according to  claim 7 .