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Castor oil‐derived plasticizers. Some nitrogen‐containing derivatives as plasticizers for vinyl chloride‐vinyl acetate copolymer and cellulose acetate resins
Author(s) -
Magne Frank C.,
Dupuy Harold P.,
Goldblatt Leo A.
Publication year - 1959
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/bf02640274
Subject(s) - morpholine , plasticizer , vinyl acetate , octadecane , chemistry , vinyl chloride , ricinoleic acid , organic chemistry , cellulose acetate , castor oil , polymer chemistry , copolymer , cellulose , polymer
Summary Eight nitrogen‐containing derivatives of ricinoleic acid, namely, 4‐ricinoleoylmorpholine, 4‐(12‐hydroxystearoyl) morpholine, 4‐(12‐acetoxyoleoyl) morpholine, 4‐(12‐acetoxystearoyl) morpholine, 4‐(12‐β‐cyanoethoxyoleoyl) morpholine, 4‐(12‐β‐cyanoethoxystearoyl) morpholine, 1,12‐bis(β‐cyanoethoxy)‐9‐octadecene, and 1,12‐bis(β‐cyanoethoxy)octadecane were screened for their plasticizer characteristics. 1,12‐Diacetoxy‐9‐octadecene and 1,12‐diacetoxyoctadecane were also screened to compare cyanoethylated with acetylated derivatives. All of these materials, except 4‐(12‐hydroxystearoyl)morpholine, were found to be satisfactory primary plasticizers for vinyl chloride‐vinyl acetate copolymer. In general, these derivatives are quite similar to di(2‐ethylhexyl) phthalate in plasticizing performance. However 1,12‐bis(β‐cyanoethoxy)‐9‐octadecene and 1,12‐bis(β‐cyanoethoxy)octadecane have exceptionally good low‐temperature properties. It was also found that 4‐ricinoleoylmorpholine, 4‐(12‐acetoxyoleoyl)morphine, 4‐(12‐β‐cyanoethoxyoleoyl)morpholine, and 4‐(12‐β‐cyanoethoxystearoyl)morpholine were satisfactory plasticizers for cellulose acetate.