Syntheses of semicrystalline aromatic poly(thioether thioether ketone)s (PTTK and PTBTK) and their copolymers with ether analogues

Yong Ding, Antisar R. Hlil, Allan S. Hay*, Eishun Tsuchida, Kenji Miyatake

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)


One-pot polymerization between bis(N,N′-dimethyl-S-carbamate)s and activated dihalo compounds was extended to the synthesis of semicrystalline poly(arylene thioether)s as well as their copolymers. Aromatic poly(thioether thioether ketone) (PTTK) and poly(thioether biphenyl thioether ketone) (PTBTK) were synthesized from 4,4′-difluorobenzophenone and bis(N,N′-dimethyl-S-carbamate)s prepared from hydroquinone and 4,4′-biphenol via the Newman-Kwart rearrangement reaction, respectively. Random copolymers were prepared by copolymerization of 4,4′-difluorobenzophenone with a mixture of bis(N,N′-dimethyl-S-carbamate)s or with a bis(N,N′-dimethyl-S-carbamate) and hydroquinone or 4,4′-biphenol. The reactions were carried out in benzophenone solution in the presence of a mixture of Cs2CO3 and CaCO3 as the bases at polymerization temperatures ranging from 200 to 300°C in order to keep the products in solution. All the polymers obtained were semicrystalline, as evidenced from the sharp melting points from the DSC scans for the polymers as prepared. However, the crystallization speeds for these polymers are very different depending on the compositions. The relationships between Tg, Tm, and structures are discussed. PTTK has a Tg of 136°C, Tm of 304°C, and an inherent viscosity of 0.32 dL/g in concentrated sulfuric acid, while PTBTK has a Tg of 173°C, Tm of 351°C, and an inherent viscosity of 0.46 dL/g.

Original languageEnglish
Pages (from-to)315-321
Number of pages7
Issue number2
Publication statusPublished - 1999 Jan 26

ASJC Scopus subject areas

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


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