Synthesis and Characterization of Organo-Soluble Polyimides Derived from Alicyclic Dianhydrides and a Dihydroxyl-Functionalized Spirobisindane Diamine
KAUST DepartmentFunctional Polymer Membranes Group, Advanced Membranes and Porous Materials Center, Division of Physical Sciences and Engineering, King Abdullah University of Science and Technology (KAUST), Thuwal 23955, Saudi Arabia
Biological and Environmental Sciences and Engineering (BESE) Division
Advanced Membranes and Porous Materials Research Center
Physical Science and Engineering (PSE) Division
Chemical Engineering Program
KAUST Grant NumberBAS/1/1323-01-01
Permanent link to this recordhttp://hdl.handle.net/10754/668694
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AbstractTwo organo-soluble polyimides were synthesized by reaction of alicyclic bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride (BC) or 1,4,7,8-tetrabromobicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic anhydride (BCBr4) with 3,3,3′,3′-tetramethyl-1,1′-spirobisindane-5,5′-diamino-6,6′-diol (SBIDA). BC–SBIDA and BCBr4–SBIDA showed thermal stability of up to ∼420 and 352 °C and displayed microporosity as indicated by Brunauer–Emmett–Teller surface areas of 191 and 243 m2 g–1, respectively. The polyimides were solution-processable in polar organic solvents and exhibited strong mechanical properties with tensile modulus of 1.15–1.4 GPa, tensile strength of 27–28 MPa, and elongation at break of 2–4%. Introducing alicyclic moieties disturbs the delocalization of π-electrons across the polyimide backbone that reduces formation of charge transfer complexes (CTCs) leading to formation of colorless and transparent polyimide films. A fresh film sample of the bromine substituted BCBr4–SBIDA showed oxygen permeability of 31 barrer and oxygen/nitrogen selectivity of 5.9. Long-term physical aging of BCBr4–SBIDA over 365 days resulted in decrease of O2 permeability to 17 barrer with a simultaneous boost in O2/N2 selectivity to 6.6, which demonstrated highly competitive performance compared to commercially available polymers for air separation.
CitationAbdulhamid, M. A., Ma, X., Ghanem, B. S., & Pinnau, I. (2018). Synthesis and Characterization of Organo-Soluble Polyimides Derived from Alicyclic Dianhydrides and a Dihydroxyl-Functionalized Spirobisindane Diamine. ACS Applied Polymer Materials, 1(1), 63–69. doi:10.1021/acsapm.8b00036
SponsorsThis work was supported by funding (BAS/1/1323-01-01) from King Abdullah University of Science and Technology (KAUST).
PublisherAmerican Chemical Society (ACS)
JournalACS Applied Polymer Materials