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 language | English |
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Pages (from-to) | 272-278 |
Number of pages | 7 |
Journal | Polymer Journal |
Volume | 43 |
Issue number | 3 |
DOIs | |
Publication status | Published - Mar 2011 |
Externally published | Yes |
Keywords
- azidation
- azidopolyester
- diphenylphosphoryl azide (DPPA)
- photo-crosslinking
- polycondensation
- sodium azide (NaN)
- water-soluble polyester
ASJC Scopus subject areas
- Polymers and Plastics
- Materials Chemistry