CHa( CHz)?CH-CH( CHz)&OOCH&H=CH2 Allyl epoxystearate

‘d \O/

CHs(CH~)7CH-CH(CH~)7CH200CCH=CH=CH~ Epoxystearyl acrylate

The flux time for epoxystearyl acry- late was slower than for allyl epoxy- stearate (Table 111). This may indicate some polymerization of the easily poly- merizable acrylic ester, because the polymer is expected to flux more slowly than the monomer.

After 5 months of exposure to north window light these two products showed no tack. After the accelerated light exposure test the allyl epoxystearate compound had a slight spew, the epoxy- stearyl acrylate compound had de- veloped a heavy spew and noticeably increased in stiffness. This may have been caused by further light-catalyzed polymerization of the reactive acrylate ester.

Tensile strengths for the two com- pounds were comparable (Table 111). Efficiency and elongation were better for the compound containing allyl epoxystearate, and low temperature flexibility was somewhat better. This is probably a further indication of poly- merization during milling of the epoxy- stearyl acrylate system.

Gasoline extraction losses were com- parable. Mineral oil extraction losses were slightly higher in the case of allyl epoxystearate; soapy water extraction losses were appreciably higher. If poly- merization occurred during milling of epoxystearyl acrylate, one might ex- pect the polymer to have better extrac- tion properties than the monomer. A product made by externally polymeriz- ing epoxystearyl acrylate using a vinyl polymerization catalyst showed very poor compatibility with poly(viny1 chlo- ride). This high viscosity oil had nearly the same oxirane content as the corre- sponding monomer. Volatilities shown by the activated carbon test were com- parable.

The vinyl stock plasticized with allyl epoxystearate had excellent color stability in the oven heat test. Epoxystearyl acry- late produced a hazy film after 15 min- utes of exposure a t this temperature. This difference is probably accounted for by the greater tendency of epoxystearyl acrylate to polymerize and lose compati- bility.

All three samples were free from exuda- tion after 3 months of exposure to north window light. After 5 months, vinyl epoxystearate showed a slight spew; the other two compounds showed no spew. I n the accelerated exposure test, compounds containing epoxystearyl ace- tate and ethyl epoxystearate remained free from surface spew; the vinyl epoxystearate compound developed a heavy exudation and the stock became stiff.

Tensile strengths of epoxystearyl ace- tate and ethyl epoxystearate were com- parable and a little lower than that of vinyl epoxystearate (Table 111). The efficiency of vinyl epoxystearate was inferior to those of ethyl epoxystearate or epoxystearyl acetate. The low tem- perature flexibilities of epoxystearyl acetate and ethyl epoxystearate were comparable and superior to that of vinyl epoxystearate. These differences would be expected if polymerization of vinyl epoxystearate had occurred.

Gasoline and oil extraction losses were comparable. Soapy water extraction losses were high in all three cases.

Volatilities of all three samples were relatively high, as anticipated from their lower molecular weight compared with materials described previously.

The vinyl epoxystearate plasticized film possessed poor heat stability, as it became dark and cloudy after 15 minutes. Both ethyl epoxystearate and epoxystearyl acetate plasticized films had excellent heat stability. The defi- ciency of the vinyl ester may be due to polymerization of vinyl epoxystearate under test conditions.

Epoxidized counterparts based on butyl oleate and butyl elaidate were com- pared.

CHa(C\H2)7 >CHz)7COOBu

‘c-c’ ”‘0’ \

cis H (CHZ)~COOBU \ / c-c /\qH

CH3(CHz)? 0

trans

CHI( CHz),CH-CH( CH~)?COOCH=CHZ Vinyl epoxystearate

‘O/

‘0’

CH3( CHl)7CH-CH( CHz)?COOCH&H3 Ethyl epoxystearate

CHs( CHZ)~CH-CH(CH~)?CH~OOCCH* Epoxystearyl acetate

Epoxidized butyl elaidate stock showed a slight waxy exudation after aging in the dark for a few days. Epoxidized butyl oleate stock showed no exudation after aging 5 months exposed to north window light. Tests were run on the epoxidized butyl elaidate stock in spite of this slight waxy exudation.

Differences in tensile strength, elonga- tion, and moduli between the elaidate and oleate counterparts were small (Table 111).

Low temperature flexibility was ap- preciably poorer (Tf, -37.8’ C.) for epoxidized butyl elaidate than for epoxi- dized butyl-oleate (T,, - 46.2 ’ C.). The trans isomer is somewhat higher in melting point. Heat stabilities of the two products were comparable and very good.

Gasoline and mineral, oil extraction losses were higher for the elaidic acid- than for the oleic acid-based product. These variations could be due to dif- ferences in compatibility.

Literature Cited

Archer-Daniels-Midland Co., hlinne- apolis, Minn., Tech. Paper 152.

Durbetaki, A. J., Anal. Chem. 20, 2000 (1956).

E. I. du Pont de Nemours & Co., Inc., Per-oxygen Products Bull. P61-454.

Mueller, A. C. (to Shell Development Co.), U. S. Patent 2,772,296 (Nov. 11, 1956).

Swern, D., Knight, H., Shreve, O., Heether. hl.. J . Am. Oil Chemists Soc. 27, i 7 (1950).

RECEIVED for review February 13, 1958 ACCEPTED March 29, 1958

Division of Paint, Plastics, and Printing Ink Chemistry, Epoxy Plasticizers-Stabilizers Symposium, 132nd Meeting, ACS, New York, N. Y., September 1957.

Recovering Fission Products- Correction

In the article on “Recovering Fission Products” [Barton, G. B., Hepworth, J. L., McClanahan, E. D., Jr., Moore, R. L., Van Tuyl, H. H., IKD. ENG. CHEY. 50, 21 2 (1 958) 1, the following errors occurred.

Table I, page 214. Footnote‘ refers to Precipitant, and should read: 2.5M nitric acid, 10-41M cesium. 0.1M urea present in ferrocyanide experiments.

Table VI, first column, Rb, not Ru. Second column, NH4 concentration should have been given as 0.1. Sixth column, fourth numerical entry should have been given as 0.00005 (not 0.0005) and last entry as 0.0001. The head- ing of the seventh column should be Zn and Fe(CN)6-4M. I n the eighth col- umn, the last entry should have been 14.

870 INDUSTRIAL A N D ENGINEERING CHEMISTRY