Effect of Structure of Epoxidized Esters on the Physical Properties of Their Phthalic Anhydride Cured Resins.

Fette, Seifen, Anstrichm.

Maerker

1961

Die voi-ca. 20 Jahren mit dem Ziel begonnenen Forschungsarbeiten des Eastern Regional Research Laboratory, Philadelphia, genuBuntaugliche Tierfette durch cheinische Behandlung in technische ,,Oleochemikalien" zu verwandeln und ihnen darnit einen groljeren Absatzniarkt zu verschaffen, haben zu betrdchtlichen Erfolgen gefiihrt. Die geradkettigen unverzweigten Fettsauren ldssen sich in zahlreiche Derivate uberfuhren, die fur die Herstellung yon Kunststoffen, wahrscheinlich auch van Schmiermitteln, von Wert sind.

Über die Verwendung der Tierfette

Fette, Seifen, Anstrichm.

Maerker

1961

Rearrangement of epoxy fatty esters to keto fatty esters

Walens

Koob

et al. 1965

J Americ Oil Chem Soc

The rearrangement of fatty epoxyesters to ketoesters was studied. The isomerization is carried out in nonaqueous media and is catalyzed by acids. Esters containing one epoxy group per fatty acid chain are isomerized to the corresponding ketones in 70舑90% yields using boron fluoride etherate catalyst in boiling dioxane. Conversion to ketonic products is measured either by chromatographic separation followed by IR analysis or by oximation. Principal byproducts are hydroxy derivatives. Fatty esters containing more than one epoxy group/fatty acid chain give low ketone yields.

Epoxy resins from fatty esters derived from cyclohexane and epoxycyclohexane

Scholnick

Port

1963

J Americ Oil Chem Soc

The magnitude of the physical properties of resins obtained by the phthalic anhydride cure of non‐terminal epoxy monomers, prepared from fatty derivatives, was shown to be dependent on the distribution of the epoxy groups in the monomer. The monomers were prepared by epoxidizing a series of unsaturated esters, selected to test the effect of the addition of a single symmetrically disposed epoxide group. Oleoyl and linoleoyl esters of tetrahydrophthalyl alcohol, as well as dioleyl and dilinoleyl tetrahydrophthalate, were epoxidized and cured with phthalic anhydride (Group A). For comparison, epoxy monomers were prepared from oleoyl and linoleoyl esters of hexahydrophthalyl alcohol, as well as dioleyl and dilinoleyl hexahydrophthalate (Group B). When these epoxides were cured with phthalic anhydride, it was found that the resins derived from Group A had heat distortion temperatures which were approximately 55舑65C higher than those from Group B.