Biobased carbodiimides, a process for preparation thereof and use thereof

Abstract

The present invention relates to novel biobased carbodiimides, a process for production thereof and use thereof. The biobased carbodiimides according to the invention comprise the reaction product of at least one carbodiimide and a carbon acid compound isolated or produced from renewable raw materials and having a functionality >1 and/or a hydroxy carboxylic ester having 2-24 carbon atoms.

What is claimed is: 
     
         1 . Biobased carbodiimides obtainable from the reaction of at least one carbodiimide and at least one carbon acid compound isolated or produced from renewable raw materials and having a functionality >1 and more than 4 carbon atoms and/or a hydroxy carboxylic ester having 2-24 carbon atoms. 
     
     
         2 . Biobased carbodiimides according to  claim 1 , characterized in that the carbodiimide comprises a compound of formula (1)
   R′—(—N═C═N—R—) m —R   (I)
   where   R represents an aromatic, aliphatic, cycloaliphatic or araliphatic radical which in the case of an aromatic or araliphatic radical may bear aliphatic and/or cycloaliphatic substituents having at least two carbon atoms in at least one position ortho to the aromatic carbon atom bearing the carbodiimide group,   R′=C 1 -C 18 -alkyl, C 5 -C 18 -cycloalkyl, aryl, C 7 -C 18 -aralkyl or R—NCO, R—NHCONHR 1 , R—NHCONR 1 R 2  or R—NHCOOR 3 , and   R″ denotes —NCO,   where, in R′, R 1  and R 2  are each independently the same or different and signify a C 1 -C 6 -alkyl, C 6 -C 10 -cycloalkyl or C 7 -C 18 -aralkyl radical and R 3  has one of the meanings of R 1  or denotes a polyester or polyamide radical,   and   m is an integer from 1 to 5000 and preferably from 1 to 500.   
     
     
         3 . Biobased carbodiimides according to  claim 1  or  2 , characterized in that the carbodiimide comprises a compound of formulae (II)-(III) 
       
         
           
           
               
               
           
         
         where x=1 to 50, 
       
       
         
           
           
               
               
           
         
         where y=1 to 20 
       
       and/or isophorone diisocyanate and/or dicyclohexylmethane 4,4′-diisocyanate (H12-MDI=hydrogenated MDI). 
     
     
         4 . Biobased carbodiimides according to any one of  claims 1  to  3 , characterized in that the hydroxy carboxylic ester comprises one or more polyhydroxybutyrates of formula (IV) 
       
         
           
           
               
               
           
         
         where n=2-20. 
       
     
     
         5 . Biobased carbodiimides according to any one of  claims 1  to  4 , characterized in that the ratio of the carbodiimide to the carbon acid compound and/or the hydroxy carboxylic ester is in the range from 5:95 to 95:5. 
     
     
         6 . Biobased carbodiimides according to any one of  claims 1  to  5 , characterized in that they additionally contain non-biobased polyols based on polyether, polyester and/or polyetherester. 
     
     
         7 . Process for producing the biobased carbodiimides according to any one of  claims 1  to  6 , characterized in that at least one carbodiimide is reacted with at least one carbon acid compound isolated or produced from renewable raw materials and having a functionality >1 and/or the hydroxy carboxylic ester and optionally non-biobased polyols based on polyether, polyester and/or polyetherester at temperatures between 20 and 200° C. in solution and/or in the absence of a solvent in the presence or absence of a catalyst. 
     
     
         8 . Use of the biobased carbodiimides according to any one of  claims 1  to  6  in polyurethane applications, for rigid foam/coatings, flexible foam, CASE (Coatings Adhesives, Sealants, Elastomers), thermoplastics, in lubricant applications, in transformer oils for hydrolysis control and for crosslinking of polyurethanes.