Summary
Thirty-one acyloxy or aryloxy esters prepared from hydroxystearic acids have been evaluated as plasticizers for a vinyl chloride-vinyl acetate copolymer (95∶5). Many of them were found to be primary plasticizers, having outstanding low-temperature performance when employed at the 35% level. Formulations with these compounds compared quite favorably in tensile properties with those containing the di-2-ethylhexyl esters of phthalic, sebacic, azelaic, and adipic acids. Volatility losses were similar to those of the four di-2-ethylhexyl esters. The loss of plasticizer through migration was equal to or less than that from compositions containing the esters of sebacic, azelaic, and adipic acids but was greater than that of the phthalate ester.
A mechanistic scheme of plasticizer-polymer interaction has been presented, proposing that the rate of diffusion of plasticizer through the polymer mass is a controlling factor in both good low-temperature performance and the resulting high migration losses. Methyl esters, some aromatic esters, and esters containing three or more polar centers have improved permanence but show a more rapid change in torsional modulus as the temperature is lowered during the determination of the Clash-Berg stiffening temperature.
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References
Alfrey, T. Jr., “Mechanical Behavior of High Polymers”, Interscience Publishers Inc., New York (1948).
Am. Soc. Testing Materials, Philadelphia, Standards, ASTM D 412-51T.
Am. Soc. Testing Materials, Philadelphia, Standards, ASTM D 882-56T.
Am. Soc. Testing Materials, Philadelphia, Standards, ASTM D 1043-51.
Am. Soc. Testing Materials, Philadelphia, Standards, ASTM D 1203-55.
Olash, R. F. jr., and Berg, R. M., Ind. Eng. Chem.,34, 1218 (1942).
Doolittle, A. K., “The Technology of Solvents and Plasticizers,” John Wiley and Sons Inc., New York (1954).
FLAT Beport 861, “Plasticizers for Polyvinyl Chloride,” July 23, 1946.
Geenty, J. R., India Rubber World,126, 646 (1952).
Greenspan, F. P., and Gall, R. J., Ind. Eng. Chem.,45, 2722 (1953).
Gruber, W., and Machemer, H., U. S. 2,332,849, Oct. 26, 1943.
Hunter, M. J., and Kropscott, E. L., U. S. 2,385,359, Sept. 25, 1945.
Kadesch, R. G., Modern Plastics,29, No. 12, 111 (1952).
Knight, H. B., Koos, R. E., and Swern, Daniel, J. Am. Oil Chemists' Soc.,31, 1 (1954).
Lawrence, R. R., and McIntyre, E. B., Ind. Eng. Chem.,41, 689 (1949).
Magne, F. C., and Mod, R. R., J. Am. Oil Chemists' Soc.,30, 269 (1953).
Mead, D. J., Tickenor, R. L., and Fuoss, R. M., J. Am. Chem. Soc.,64, 283 (1942).
Teeter, H. M., and Cowan, J. C., U. S. 2,652,411, Sept. 15, 1953; Teeter, H. M., Gast, L. E., Bell, E. W., and Cowan, J. C., Ind. Eng. Chem.45, 1777 (1953); Gast, L. E., Croston, C. B., Schneider, W. J., and Teeter, H. M.,ibid., 46, 2205 (1954).
Witnauer, L. P., Knight, H. B., Palm, W. E., Koos, R. E., Ault, W. C., and Swern, Daniel, Ind. Eng. Chem.,47, 2304 (1955).
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Eastern Utilization Research and Development Division, Agricultural Research Service, U. S. Department of Agriculture.
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Knight, H.B., Witnauer, L.P., Palm, W.E. et al. Esters of hydroxystearic acids as primary low-temperature plasticizers for a vinyl chloride—Vinyl acetate copolymer. J Am Oil Chem Soc 36, 382–388 (1959). https://doi.org/10.1007/BF02639611
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DOI: https://doi.org/10.1007/BF02639611