Synthesis and characterization of poly(urethane‐sulfone)s

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Eight poly(urethane‐sulfone)s were synthesized from two sulfone‐containing diols, 1,3‐bis(3‐hydroxypropylsulfonyl)propane (Diol‐333) and 1,4‐bis(3‐hydroxypropylsulfonyl)butane (Diol‐343), and three diisocyanates, 1,6‐hexamethylene diisocyanate (HMDI), 4,4′‐diphenylmethane diisocyanate (MDI), and tolylene diisocyanate (TDI, 2,4‐ 80%; 2,6‐20%). As a comparison, eight polyurethanes were also synthesized from two alkanediols, 1,9‐nonanediol and 1,10‐decanediol, and three diisocyanates. Diol‐333 and Diol‐343 were prepared by the addition of 1,3‐propanedithiol or 1,4‐butanedithiol to allyl alcohol and subsequent oxidation of the resulting sulfide‐containing diols. The homopoly(urethanesulfone)s from HMDI and MDI are semicrystalline, and are soluble in m‐cresol and hot DMF, DMAC, and DMSO. The copoly(urethane‐sulfone)s from a 1/1 molar ratio mixture of Diol‐333 and Diol‐343 with HMDI or MDI have lower crystallinity and better solubility than the corresponding homopoly(urethane‐sulfone)s. The poly(urethane‐sulfone)s from TDI are amorphous, and are readily soluble in m‐cresol, DMF, DMAC, and DMSO at room temperature. Differential scanning calorimetry data showed that poly(urethane‐sulfone)s have higher glass transition temperatures and melting points than the corresponding polyurethanes without sulfone groups. The rise in glass transition temperature is 20–25°C while the rise in melting temperature is 46–71°C.