Azidation of polyesters having pendent functionalities by using NaN 3 or DPPA-DBU and photo-crosslinking of the azidopolyesters

Yosuke Shibata, Hiroki Tanaka, Akinori Takasu, Yasuhiko Hayashi

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

In this article, we performed dehydration polycondensation of bromosuccinic acid and methylsuccinic acid with 1,4-butanediol at 80°C to synthesize aliphatic polyesters containing pendent bromo groups without dehydrobromination using scandium trifluoromethanesulfonate (Sc(OTf)3) as the catalyst. Azidation of the resultant polyesters was carried out readily in N,N-dimethylformamide at room temperature using sodium azide (Mn = 8.3 × 103 (Mw/Mn = 2.17)). 1H nuclear magnetic resonance analysis of the product revealed that 65% contained azide functionality, and dehydrobromination occurred in 35% during the azidation process. On the other hand, azidation of poly(butylene bromoadipate-co-butylene methylsuccinate) (poly(BBA-co-BMS)) proceeded successfully under the same conditions to generate poly(butylene azidoadipate-co-butylene methylsuccinate) (poly(BAA-co-BMS)) without dehydrobromination (Mn = 10.4 × 103 (Mw/Mn = 2.71)). We successfully photo-crosslinked the resultant azidopolyester by ultraviolet irradiation and examined it using scanning electron microscope. We also described azidation of polyesters having pendent hydroxyl groups by using the DPPA (diphenylphosphoryl azide)-DBU (1,8-diazabicyclo5.4.0undec-7-ene) substitution strategy to produce water-soluble polyesters containing pendent azido groups (Mn = 7.5 × 103 (Mw/Mn = 2.25)). These azidopolyesters might be extremely useful not only for their derivatization by simple chemical modification but also for their effective utilization as photolithography material.

Original languageEnglish
Pages (from-to)272-278
Number of pages7
JournalPolymer Journal
Volume43
Issue number3
DOIs
Publication statusPublished - Mar 2011

Keywords

  • azidation
  • azidopolyester
  • diphenylphosphoryl azide (DPPA)
  • photo-crosslinking
  • polycondensation
  • sodium azide (NaN)
  • water-soluble polyester

ASJC Scopus subject areas

  • Polymers and Plastics
  • Materials Chemistry

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