Hydroxy-terminated polyesters were synthesized by treating diols with the diethyl esters of dicarboxylic acids. Ethylene, diethylene, and triethylene glycols, four polyoxyethylene glycols ranging in molecular weight from 200 to 600, 1,2-propanediol, dipropylene glycol, five polyoxypropylene glycols ranging in molecular weight from 150 to 2025, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,5-pentanediol, 2,2′-(methylimino)diethanol, 2,2′-(ethylimino)diethanol, 2,2′-(butylimino)diethanol, and 2,2′-thiodiethanol were condensed with diethyl succinate in the absence and presence of a catalyst, and with diethyl cyanomalonate, cyanosuccinate, and α-cyanoglutarate.Polyurethanes were obtained from the various polyesters prepared by treatment with different quantities of 2,4-tolylene diiocyanate. In general, non-elastomeric products were obtained from polyesters of monomeric glycols, while elastomeric polyurethanes with the lowest brittle points were formed from polyoxyethylene glycol 400 and 600, and polyoxypropylene glycol 750, 1025, and 2025 polyesters. Also the succinate polyurethanes, which did not contain nitrile groups, had the greatest tendency to be elastomeric and had the lowest brittle points. For the nitrile containing polyurethanes, the cyanomalonates had the lowest tendency to be elastomeric and had the highest brittle points. The cyanosuccinate and α-cyanoglutarates had about the same properties.
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