Synthesis and gas permeation properties of poly(diphenylacetylenes) having bulky alkyl/silyl and hydroxy groups

Journal of Membrane Science

Volumn 282, Issue 1-2, 2006, Pages 423-429

  Hu, Yanming ^a   Sakaguchi, Toshikazu ^a   Shiotsuki, Masashi ^a   Sanda, Fumio ^a   Masuda, Toshio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Desilylation; Diphenylacetylene; Gas permeability

Indexed keywords

CHEMICAL BONDS; GAS PERMEABLE MEMBRANES; MECHANICAL PERMEABILITY; MOLECULAR WEIGHT; MONOMERS; PARAFFINS; SYNTHESIS (CHEMICAL);

DESILYLATION; DIPHENYLACETYLENE; GAS PERMEABILITY; TRIFLUOROACETIC ACID (TFA);

ORGANIC POLYMERS;

ACETYLENE DERIVATIVE; BUTYLATED HYDROXYANISOLE; CARBON; CARBON DIOXIDE; CYCLOHEXANE; HEXANE; HYDROGEN; HYDROXYACID; NITROGEN; POLYMER; SILANE DERIVATIVE; SILICON; SOLVENT; TANTALUM; TIN; TOLUENE; TRIFLUOROACETIC ACID;

CHEMICAL BONDS; GAS PERMEABLE MEMBRANES; MECHANICAL PERMEABILITY; MOLECULAR WEIGHT; MONOMERS; ORGANIC POLYMERS; PARAFFINS; SYNTHESIS (CHEMICAL);

ARTICLE; DESILYLATION; GAS PERMEABILITY; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS; THERMAL ANALYSIS; THERMOGRAVIMETRY;

EID: 33747777756     PISSN: 03767388     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.memsci.2006.06.001     Document Type: Article

References (29)

1. Masuda T., and Sanda F. Polymerization of substituted acetylenes. In: Grubbs R.H. (Ed). Handbook of Metathesis vol. 3 (2003), Wiley-VCH, Weinheim 375-406 Chapter 3.11
2. Nomura R., and Masuda T. In: Kroshwitz J.I. (Ed). Encyclopedia of Polymer Science and Technology (2003), Wiley, New York
3. Choi S.K., Gal Y.S., Jin S.H., and Kim H.K. Poly(1,6-heptadiyne)-based materials by metathesis polymerization. Chem. Rev. 100 (2000) 1645-1682
4. Nagai K., Masuda T., Nakagawa T., Freeman B.D., and Pinnau I. Poly[1-(trimethylsilyl)-1-propyne] and related polymers: synthesis, properties and functions. Prog. Polym. Sci. 26 (2001) 721-798
5. Koros W.J., and Mahajan R. Pushing the limits on possibilities for large scale gas separation: which strategies. J. Membr. Sci. 175 (2000) 181-196
6. Aoki T. Macromolecular design of permselective membranes. Prog. Polym. Sci. 24 (1999) 951-993
7. Masuda T., Isobe E., and Higashimura T. Poly[1-(trimethylsilyl)-1-propyne]: a new high polymer synthesized with transition-metal catalysts and characterized by extremely high gas permeability. J. Am. Chem. Soc. 105 (1983) 7473-7474
8. Masuda T., Isobe E., and Higashimura T. Polymerization of 1-(trimethylsilyl)-1-propyne by halides of niobium(V) and tantalum(V) and polymer properties. Macromolecules 18 (1985) 841-845
9. Tsuchihara K., Masuda T., and Higashimura T. Tractable silicon-containing poly(diphenylacetylenes): their synthesis and high gas permeability. J. Am. Chem. Soc. 113 (1991) 8489-8548
10. Tsuchihara K., Masuda T., and Higashimura T. Polymerization of silicon-containing diphenylacetylenes and high gas permeability of the product polymers. Macromolecules 25 (1992) 5816-5820
11. Kouzai H., Masuda T., and Higashimura T. Synthesis and properties of poly(diphenylacetylenes) having aliphatic para-substituents. J. Polym. Sci. Polym. Chem. 32 (1994) 2523-2530
12. Teraguchi M., and Masuda T. Poly(diphenylacetylene) membranes with high gas permeability and remarkable chiral memory. Macromolecules 35 (2002) 1149-1151
13. Sakaguchi T., Yumoto K., Shiotsuki M., Sanda F., Yoshikawa M., and Masuda T. Synthesis of poly(diphenylacetylene) membranes by desilylation of various precursor polymers and their properties. Macromolecules 38 (2005) 2704-2709
14. Shida Y., Sakaguchi T., Shiotsuki M., Wagenar K.B., and Masuda T. Preparation and properties of polytolan membranes bearing p-hydroxyl groups. Polymer 46 (2005) 1-4
15. Shida Y., Sakaguchi T., Shiotsuki M., Sanda F., Freeman B.D., and Masuda T. Synthesis and properties of poly(diphenylacetylenes) having hydroxyl groups. Macromolecules 38 (2005) 4096-4102
16. Dai Y., Guiver M.D., Robertson G.P., Kang Y.S., Lee K.J., and Jho J.Y. Preparation and characterization of polysulfones containing both hexafluoroisopropylidene and trimethylsilyl groups as gas separation membrane materials. Macromolecules 37 (2004) 1403-1410
17. Kim Y.H., Kim H.S., and Kwon S.K. Synthesis and characterization of highly soluble and oxygen permeable new polyimides based on twisted biphenyl dianhydride and spirobifluorene diamine. Macromolecules 38 (2005) 7950-7956
18. Ayala D., Lozano A.E., Abajo J., Perez C., Campa J.G., Peinemann K.V., Freeman B.D., and Prabhakar R. Gas separation properties of aromatic polyimides. J. Membr. Sci. 215 (2003) 61-73
19. Kim Y.H., Ahn S.K., Kim H.S., and Kwon S.K. Synthesis and characterization of new organosoluble and gas-permeable polyimides from bulky substituted pyromellitic dianhydrides. J. Polym. Sci. Polym. Chem. 40 (2002) 4288-4296
20. Orme C.J., Klaehn J.R., and Stewart F.F. Gas permeability and ideal selectivity of poly[bis-(phenoxy)phosphazene], poly[bis-(4-tert-butylphenoxy)phosphazene], and poly[bis-(3,5-di-tert-butylphenoxy)1.2(chloro)0.8 phosphazene]. J. Membr. Sci. 238 (2004) 47-55
21. Handa Y.P., Roovers J., and Moulinié P. Gas transport properties of substituted PEEKs. J. Polym. Sci. Polym. Phys. 35 (1997) 2355-2362
22. Aoki T., Nakahara H., Hayakawa Y., Kokai M., and Oikawa E. Trimethylsilyl-group containing polyphenylacetylenes for oxygen and ethanol permselective membranes. J. Polym. Sci. Polym. Chem. 32 (1994) 849-858
23. Sonogashira K. Development of Pd-Cu catalyzed cross-coupling of terminal acetylenes with sp2-carbon halides. J. Organomet. Chem. 653 (2002) 46-49
24. Suzuki T., Sato E., Unno K., and Kametani T. Enantioselective synthesis of trans-octahydro-1,6-dioxoinden-4-ylpropionic acid from (R)-2,3-O-isopropylideneglyceraldehyde by tandem orthoester Claisen rearrangement. J. Chem. Soc. Perkin Trans. 1 (1986) 2263-2268
25. Lin H., and Freeman B.D. Gas solubility, diffusivity and permeability in poly(ethylene oxide). J. Membr. Sci. 239 (2004) 105-117
26. Pixton M.R., and Paul D.R. Relationships between structure and transport properties for polymers with aromatic backbones. In: Paul D.R., and Yampolskii Y.P. (Eds). Polymeric Gas Separation Membranes (1994), CRC Press, Boca Raton, FL 83-153
27. van Krevelen D.W. Properties of Polymers: their Correlation with Chemical Structure; their Numerical Estimation and Prediction from Additive Group Contributions. 3rd ed. (1990), Elsevier Science, Amsterdam pp. 71-107
28. Bondi A. In: Boyer R.F. (Ed). Physical Properties of Molecular Crystals, Liquids, and Glasses (1968), John Wiley and Sons, New York 25-97
29. Robeson L.M. Correlation of separation factor versus permeability for polymeric membranes. J. Membr. Sci. 62 (1991) 165-185