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Preparation and plasticizing characteristics of a series of symmetrical and unsymmetrical N,N‐Disubstituted oleamides
Author(s) -
Magne Frank C.,
Mod Robert R.,
Skau Evald L.
Publication year - 1967
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/bf02639265
Subject(s) - plasticizer , substituent , alkyl , chemistry , polymer chemistry , compatibility (geochemistry) , organic chemistry , materials science , composite material
Thirty‐five N,N‐disubstituted oleamides, mostly dialkyl oleamides, have been prepared and evaluated as plasticizers for vinyl chloride‐vinyl acetate copolymer to investigate the relative effect upon plasticizer performance of N,N‐symmetrical and unsymmetrical substitution; groups such as alkyl, cycloalkyl, benzyl, 2‐alkoxyethyl, 2‐acetoxyethyl, 2‐(3‐carbobutoxypropionlyoxy)ethyl, 2‐(3‐carbohexanoxypropionyloxy)ethyl, and cyanoethyl have been investigated in systematic combinations. The compatibility of symmetrical or unsymmetrical N,N‐dialkyl oleamides, involving normal, branched, or cyclic alkyls, is controlled by the total carbon count of the combined substituent groups rather than that of the larger group. For retention of compatibility the total carbon count must not exceed about 13 atoms. Symmetrical and unsymmetrical dialkyl oleamides of the same total alkyl carbon count do not differ significantly in their plasticizing characteristics. Acyclic N,N‐dialkyl oleamides are, with few exceptions, highly efficient plasticizers, which impart good, sebacate‐like, low‐temperature impact performance to the plastic composition. A substituent attached to the nitrogen through a secondary carbon severely impairs plasticizer efficiency and cyclic or cycloalkyl substituents are detrimental to low‐temperature performance. Substitution of an alkyl group for one of the N,N‐disymmetrical substituents has little or no effect upon low‐temperature impact performance. Many of the disubstituted oleamides impart antistatic properties to the plastic composition.