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The preparation and plasticizing characteristics of pipendides of long chain fatty acids and n‐fatty acyl derivatives of other cyclic imines
Author(s) -
Mod R. R.,
Magne F. C.,
Skau E. L.
Publication year - 1964
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf03024658
Subject(s) - organic chemistry , chemistry , plasticizer , ricinoleic acid , decanoic acid , fatty acid , castor oil
Forty‐six N‐acyl derivatives of cyclic imines have been prepared, characterized, and screened as primary plasticizers for poly (vinyl chloridevinyl acetate) copolymer. Among these were the piperidides of decanoic, palmitic, stearic, oleic, erucic, ricinoleic, epoxystearic, epoxyoleic, diepoxystearic, sebacic, pinic, cottonseed, hydrogenated cottonseed, rapeseed, Limnanthes douglasii , animal, 2‐ethylhexanoic, naphthenic, and dimer acids, as well as the N‐oleoyl derivatives of a number of substituted piperidines and other cyclic imines including pyrrolidine, piperazine, hexamethylenimme, tetrahydroquinolme, 3‐azabicyclo [3.2.2] nonane, dipyridylamine, and carbazole. In general these amides of the 5‐,6‐, and 7‐membered cyclic imines exhibited exceptionally high plasticizing efficiencies. The compatibilities observed were the best to date for fatty acid derivatives on the basis of both individual and ternary fatty acid composition‐compatibility data. Several of these amides exhibited low‐temp characteristics in the adipate plasticizer range without the adverse volatility characteristics of the adipates. There are indications that some of them have appreciable antifungal activity. It has been concluded that cyclic imines will, in general, produce fatty acid derivatives of better than average compatibility as vinyl plasticizers.