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Tall oil fatty acid‐formaldehyde derivatives and their application as vinyl plasticizers
Author(s) -
DiBella E. P.,
Green Richard,
Kraft W. M.,
Gottesman R. T.
Publication year - 1965
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/bf02541132
Subject(s) - plasticizer , chemistry , phthalate , formaldehyde , organic chemistry , degree of unsaturation , anhydrous , hydrolysis , catalysis , fatty acid , polymer chemistry
Acid‐catalyzed condensations of tall oil fatty acid and related materials with formaldehyde, in the absence of a carboxylic acid solvent, led to acidic products, lower in unsaturation, but partially polymeric due to formation of interester linkages. Hydrolysis of these linkages furnished products lower in mol wt but higher in free hydroxyl content. Some modified esters of these materials were evaluated as primary plasticizers for polyvinyl chloride by comparison with dioctyl phthalate and, when applicable, to Monsanto S409. In general, those plasticizer candidates in which free hydroxyl contents were lowered by acetylation exhibited a good overall balance of physical and permanence properties but possessed poor heat stability and borderline compatibility. A preliminary study on the acid‐catalyzed reaction of ethyl tallate with anhydrous formaldehyde gave promise that an improved alternate route to fatty acid‐formaldehyde esters could be developed.