Gas transport properties of aromatic polyamides containing adamantyl moiety

Journal of Membrane Science

Volumn 453, Issue , 2014, Pages 175-191

  Bera, Debaditya ^a   Bandyopadhyay, Parthasarathi ^a   Ghosh, Sipra ^a   Banerjee, Susanta ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Adamantyl moiety; Dielectric constant; Gas permeability; Poly(ether amide)

Indexed keywords

ACTIVATION ENERGY; AMIDES; AMINES; CARBON DIOXIDE; ETHERS; GAS PERMEABILITY; GLASS TRANSITION; MONOMERS; PERMITTIVITY; PHENOXY RESINS; TRANSPORT PROPERTIES;

ADAMANTYL MOIETY; AROMATIC POLYAMIDES; DIELECTRIC CONSTANT VALUES; GAS TRANSPORT PROPERTIES; HEXAFLUOROISOPROPYLIDENE; PERMSELECTIVITIES; POLY(ETHER AMIDE); THERMAL TECHNIQUES;

GAS PERMEABLE MEMBRANES;

AROMATIC POLYAMIDE; CARBON DIOXIDE; DIAMINE; MONOMER; POLYMER;

ARTICLE; ARTIFICIAL MEMBRANE; CARBON DIOXIDE TENSION; CHEMICAL ENVIRONMENT; CHEMICAL STRUCTURE; CRYSTALLIZATION; DECOMPOSITION; DIELECTRIC CONSTANT; DIFFUSION; GAS PERMEABILITY; GAS TRANSPORT; GEL PERMEATION CHROMATOGRAPHY; GLASS TRANSITION TEMPERATURE; HYDROGEN BOND; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOPHILICITY; OXYGEN TENSION; POLYMERIZATION; PRIORITY JOURNAL; SEPARATION TECHNIQUE; SOLUBILITY; TEMPERATURE DEPENDENCE; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY DIFFRACTION;

EID: 84888223357     PISSN: 03767388     EISSN: 18733123     Source Type: Journal    
DOI: 10.1016/j.memsci.2013.10.073     Document Type: Article

References (49)

1. Semenova S.I. Polymer membranes for hydrocarbon separation and removal. J. Membr. Sci. 2004, 231:189-207.
2. Bernardo P., Drioli E., Golemme G. Membrane gas separation: a review/state of the art. Ind. Eng. Chem. Res. 2009, 48:4638-4663.
3. Robeson L.M. The upper bound revisited. J. Membr. Sci. 2008, 320:390-400.
4. Wind J.D., Paul D.R., Koros W.J. Natural gas permeation in polyimide membranes. J. Membr. Sci. 2004, 228:227-236.
5. Henis J.M.S. Commercial and practical aspects of gas separation membranes. Polymeric Gas Separation Membranes 1994, 441-512. CRC Press, Boca Raton, FL. D.R. Paul, Y. Yampolskii (Eds.).
6. 2-philic polymers. J. Membr. Sci. 2011, 372:29-39.
7. Koros W.J., Fleming G.K. Membrane-based gas separation. J. Membr. Sci. 1993, 83:1-80.
8. Maier G. Gas separation with polymer membrane. Angew. Chem. Int. Ed. 1998, 37:2960-2974.
9. Pixton M.R., Paul D.R. Gas transport properties of adamantane-based polysulfones. Polymer 1995, 36:3165-3172.
10. Aquilar-Vega M., Paul D.R. Gas transport properties of polyphenylene ethers. J. Polym. Sci. B Polym. Phys. 1993, 31:1577-1589.
11. Banerjee S., Maier G., Dannenberg C., Spinger J. Gas permeabilities of novel poly(arylene ether)s with terphenyl unit in the main chain. J. Membr. Sci. 2004, 229:63-71.
12. Li X.G., Kresse I., Xu Z.K., Springer J. Effect of temperature and pressure on gas transport in ethyl cellulose membrane. Polymer 2001, 42:6801-6810.
13. Dasgupta B., Sen S.K., Banerjee S. Gas transport properties of fluorinated poly(ether imide) membranes containing indan moiety in the main chain. J. Membr. Sci. 2009, 345:249-256.
14. Sen S.K., Banerjee S. Gas transport properties of fluorinated poly(ether imide) films containing phthalimidine moiety in the main chain. J. Membr. Sci. 2010, 350:53-61.
15. Sen S.K., Banerjee S. Spiro-biindane containing fluorinated poly(ether imide)s: synthesis, characterization and gas separation properties. J. Membr. Sci. 2010, 365:329-340.
16. Mohr J.M., Paul D.R., Tullos G.L., Cassidy P.E. Gas transport properties of a series of poly(ether ketone) polymers. Polymer 1991, 32:2387-2394.
17. Espeso J., Lozano A.E., de la Campa J.G., de Abajo J. Effect of substituents on the permeation properties of polyamide membranes. J. Membr. Sci. 2006, 280:659-665.
18. Bandyopadhyay P., Bera D., Ghosh S., Banerjee S. Di-tert-butyl containing semifluorinated poly(etheramide)s: synthesis, characterization and gas transport properties. J. Membr. Sci. 2013, 447:413-423.
19. Bera D., Bandyopadhyay P., Dasgupta B., Banerjee S. Gas transport properties of new aromatic poly(ether amide)s containing cyclohexylidene moiety. J. Membr. Sci. 2012, 116:407-408.
20. Contreras A.P., Tlenkopatchev M.A., LoD́pez-GonzaD́lez M.M., Riande E. Synthesis and gas transport properties of new high glass transition temperature ring-opened polynorbornenes. Macromolecules 2002, 35:4677-4684.
21. Espeso J., Lozano A.E., de la Campa J.G., Yoldi I.G., de Abajo J. Synthesis and properties of new aromatic polyisophthalamides with adamantylamide pendent groups. J. Polym. Sci. A Polym. Chem. 2010, 48:1743-1751.
22. Chern Y.T., Shiue H.C., Kao S.C. Synthesis and characterization of new polyamides containing adamantyl and diamantyl moieties in the main chain. J. Polym. Sci. A Polym. Chem. 1998, 36:785-792.
23. Maya E.M., Yoldi I.G., Lozano A.E., de la Campa J.G., de Abajo J. Synthesis, characterization, and gas separation properties of novel copolyimides containing adamantyl ester pendant groups. Macromolecules 2011, 44:2780-2790.
24. Kute V., Banerjee S. Novel semi-fluorinated poly(ether imide)s derived from 4-(p-aminophenoxy)-3-trifluoromethyl-4'-aminobiphenyl. Macromol. Chem. Phys. 2003, 204:2105-2112.
25. Hyperchem, Computational Chemistry, Version 8.0, Hypercube Inc., Gainesville, Florida, 2011.
26. Yamazaki N., Higashi F., Kawabata J. Studies on reactions of the N-phosphonium salts of pyridines. XI. Preparation of polypeptides and polyamides by means of triaryl phosphites in pyridine. J. Polym. Sci. Polym. Chem. Ed. 1974, 12:2149-2154.
27. Hsiao S.H., Yang C.P., Tsai C.Y., Liou G.S. A novel class of organosoluble and light-colored fluorinated polyamides derived from 2,2'-bis(4-amino-2-trifluoromethylphenoxy)biphenyl or 2,2'-bis(4-amino-2-trifluoromethylphenoxy)-1,1'-binaphthyl. Eur. Polym. J. 2004, 40:1081-1094.
28. Kumbharkar S.C., Karadkar P.B., Kharul U.K. Enhancement of gas permeation properties of polybenzimidazoles by systematic structure architecture. J. Membr. Sci. 2006, 286:161-169.
29. Ge Z., Yang S., Tao Z., Liu J., Fan L. Synthesis and characterization of novel soluble fluorinated aromatic polyamides derived from fluorinated isophthaloyl dichlorides and aromatic diamines. Polymer 2004, 45:3627-3635.
30. Liou G.S., Yang Y.L., Su Y.O. Synthesis and evaluation of photoluminescent and electrochemical properties of new aromatic polyamides and polyimides with a kink 1,2-phenylenediamine moiety. J. Polym. Sci. A Polym. Chem. 2006, 44:2587-2603.
31. Mathews A.S., Kim I., Ha C.S. Synthesis, characterization, and properties of fully aliphatic polyimides and their derivatives for microelectronics and optoelectronics applications. Macromol. Res. 2007, 15:114-128.
32. Korshak V.V., Vinogradova S.V., Vygodskii Y.S. Cardo polymers. J. Macromol. Sci. Rev. Macromol. Chem. 1974, 11:45-142.
33. Hsiao S.H., Yang C.P., Wang S.W., Chuang M.H. Synthesis and properties of aromatic polyamides containing the cyclohexane structure. J. Polym. Sci. A Polym. Chem. 1999, 37:3575-3583.
34. Morisato A., Ghosal K., Freeman B.D., Chern R.T., Alvarez J.C., de la Campa J.G., Lozano A.E., de Abajo J. Gas separation properties of aromatic polyamides containing hexafluoroisopropylidene groups. J. Membr. Sci. 1995, 104:231-241.
35. Tanaka K., Kita H., Okamoto K., Nakamura A., Kusuki Y. Gas permeability and permselectivity in homo- and copolyimides from 3,3',4,4'-biphenyltetracarboxylic dianhydride and 3,3$PRN- and 4,4'-diaminodiphenylsulfones. Polym. J. 1990, 22:381-385.
36. Mele'ndez A., de la Campa J.G., de Abajo J. Polyisophthalamides with phenoxy pendant groups. Polymer 1988, 29:1142-1145.
37. Hsiao S.H., Chang Y.H. New soluble aromatic polyamides containing ether linkages and laterally attached p-terphenyls. Eur. Polym. J. 2004, 40:1749-1757.
38. Moe M.B., Koros W.J., Hoehn H.H., Husk G.R. Effects of film history on gas transport in a fluorinated aromatic polyimide. J. Appl. Polym. Sci. 1988, 36:1833-1846.
39. Nagel C., Günther-Schade K., Fritsch D., Strunskus T., Faupel F. Free volume and transport properties in highly selective polymer membranes. Macromolecules 2002, 35:2071-2077.
40. Pixton M.R., Paul D.R. Gas transport properties of polyarylates: substituent size and symmetry effects. Macromolecules 1995, 28:8277-8286.
41. Hirayama Y., Yoshinaga T., Kusuki Y., Ninomiya K., Sakakibara T., Tamari T. Relation of gas permeability with structure of aromatic polyimides I. J. Membr. Sci. 1996, 111:169-182.
42. Stern S.A., Liu Y., Feld W.A. Structure/permeability relationships of polyimides with branched or extended diamine moieties. J. Polym. Sci. B Polym. Phys. 1993, 31:939-951.
43. Matsumoto K., Xu P., Nishikimi T. Gas permeation of aromatic polyimides. I. Relationship between gas permeabilities and dielectric constants. J. Membr. Sci. 1993, 81:15-22.
44. Miyata S., Sato S., Nagai K., Nakagawa T., Kudo K. Relationship between gas transport properties and fractional free volume determined from dielectric constant in polyimide films containing the hexfluoroisopropylidene group. J. Appl. Polym. Sci. 2008, 107:3933-3944.
45. Stern S.A. Polymers for gas separation: the next decade. J. Membr. Sci. 1994, 94:1-65.
46. Guiver M.D., Robertson G.P., Dai Y., Bilodeau F., Kang Y.S., Lee K.J., Jho J.Y., Won J. Structural characterization and gas-transport properties of brominated matrimid polyamide. J. Polym. Sci. A Polym. Chem. 2002, 40:4193-4204.
47. Xia J., Liu S., Pallathadka P.K., Chng M.L., Chung T.S. Structural determination of Extem XH 1015 and its gas permeability comparison with polysulfone and Ultem via molecular simulation. Ind. Eng. Chem. Res. 2010, 49:12014-12021.
48. Puleo A.C., Paul D.R. The effect of degree of acetylation on gas sorption and transport behavior in cellulose acetate. J. Membr. Sci. 1989, 47:301-332.
49. Carrera-Figueiras C., Aguilar-Vega M. Gas permeability and selectivity of hexafluoroisopropylidene aromatic isophthalic copolyamides. J. Polym. Sci. B Polym. Phys. 2005, 43:2625-2638.