PREPARATION AND PLASTICIZING CHARACTERISTICS OF SOME N,N-DISUBSTITUTED AMIDES OF ERUCIC AND CRAMBE ACIDS

Twenty-nine N,N-disubstituted amides of erucic, crambe, and selectively hydrogenated crambe acids were prepared, analyzed, and screened as plasticizers for poly(vinyl chloride-vinyl acetate) copolymer (PVCA). Most of the derivatives were prepared by amidation of free acids, but the feasibility and convenience of direct aminolysis of triglycerides were demonstrated with three preparations. Potassium tert-butoxide was a more effective catalyst than sodium methoxide. With the exception of N-methyl-N-furfurylerucamide, all the erucic acid derivatives were compatible and exhibited good low-temperature performance and desirable low volatility losses with the PVCA copolymer. The crambe acid derivatives had more limited compatibilities, were more volatile, were not as good in low-temperature performances, but were somewhat more efficient. Selective hydrogenation was of limited value in relieving the compatibility problem. The crambe and erucic acid derivatives incorporating either the N,N-di-n-butyl or N,N-bis(2-alkoxyethyl) moieties imparted the best low-temperature performance, brittle points of -51° to -55° C., to PVCA compositions. © 1969, American Chemical Society. All rights reserved.