BIOBASED CARBODIIMIDES, A PROCESS FOR PREPARATION THEREOF AND USE THEREOF
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.
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.