Synthesis of Poly(iminocarbonates): Degradable Polymers with Potential Applications as Disposable Plastics and as Biomaterials

Chun Li, Joachim Kohn

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Abstract

The polymerization of diphenols with dicyanates leading to poly(iminocarbonates) has been investigated in detail. As a model system, the synthesis of poly(Bisphenol A-iminocarbonate) derived from Bisphenol A [2,2-bis(4'-hydroxyphenyl)propane] and Bisphenol A dicyanate [ 2,2-bis(4'-cyanatophenyl) propane] was systematically investigated. Bulk polycondensation was found to be unsuitable, contrary to a report in the literature. The solution polymerization of Bisphenol A and Bisphenol A dicyanate was optimized in terms of solvent, catalyst, and catalyst concentration. In THF with potassium tert-butoxide as the catalyst, molecular weights (Mw) up to 80 000 were obtained. In spite of the high sensitivity of cyanates toward hydrolysis, interfacial polymerization was found to be a feasible technique for the preparation of poly(iminocarbonates). In the presence of tetrabutylammonium bromide as a phase-transfer catalyst, molecular weights (Mw) in excess of 100 000 were achieved. The interfacial polymerization of Bisphenol A with cyanogen bromide rather than Bisphenol A dicyanate was also found to be feasible, eliminating the necessity to isolate and purify the reactive dicyanate. This finding is significant since the availability of a “one-pot” procedure could reduce the cost associated with the industrial-scale preparation of poly(iminocarbonates). In order to test the scope of the synthetic procedures, four structurally new poly(iminocarbonates) were prepared.

Original languageEnglish (US)
Pages (from-to)2029-2036
Number of pages8
JournalMacromolecules
Volume22
Issue number5
DOIs
Publication statusPublished - Sep 1 1989

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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