Thermally rearranged polybenzoxazoles membranes with biphenyl moieties: Monomer isomeric effect

Journal of Membrane Science

Volumn 450, Issue , 2014, Pages 369-379

  Comesaña Gándara, Bibiana ^a,b,c   Calle, Mariola ^a   Jo, Hye Jin ^b,c   Hernández, Antonio ^c,d   de la Campa, Jose G ^a   de Abajo, Javier ^a,c   Lozano, Angel E ^a,c   Lee, Young Moo ^b  

^a INSTITUTO DE CIENCIA Y TECNOLOGÍA DE POLÍMEROS   (Spain)

^b Hanyang University   (South Korea)

^c SMAP   (Spain)

^d UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

CO2 capture membranes; Gas separation membranes; Isomeric study; Poly(hydroxyimide)s; Thermally rearranged (TR) polymers

Indexed keywords

FILM-FORMING ABILITIES; FRACTIONAL FREE VOLUME; GAS SEPARATION MEMBRANE; HEXAFLUOROPROPANE DIANHYDRIDE (6FDA); ISOMERIC STUDY; POLY(HYDROXY-IMIDE); THERMAL REARRANGEMENT; TREATMENT TEMPERATURE;

CARBON DIOXIDE; GAS PERMEABILITY; MECHANICAL PROPERTIES; MONOMERS; POLYIMIDES; POLYMERIC FILMS;

GAS PERMEABLE MEMBRANES;

BENZOXAZOLE DERIVATIVE; BIPHENYL DERIVATIVE; DIAMINE; MONOMER; POLYIMIDE;

ARTICLE; CATALYST; CONTROLLED STUDY; GAS PERMEABILITY; GLASS TRANSITION TEMPERATURE; HEATING; HIGH TEMPERATURE; ISOMER; MASS SPECTROMETRY; MEMBRANE; MOLECULAR MODEL; NUCLEOPHILICITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE; THERMOGRAVIMETRY;

EID: 84885729179     PISSN: 03767388     EISSN: 18733123     Source Type: Journal    
DOI: 10.1016/j.memsci.2013.09.010     Document Type: Article

References (46)

1. 4 separation: a review. Int. J. Greenhouse Gas Control 2013, 12:84-107.
2. Buonomenna M.G., Yave W., Golemme G. Some approaches for high performance polymer based membranes for gas separation: block copolymers, carbon molecular sieves and mixed matrix membranes. RSC Adv. 2012, 2:10745-10773.
3. 2 separations. Energy Environ. Sci. 2012, 5:7306-7322.
4. Lau C.H., Li P., Li F., Chung T.-S., Paul D.R. Reverse-selective polymeric membranes for gas separations. Prog. Polym. Sci. 2013, 38:740-766.
5. Yampolskii Y. Polymeric gas separation membranes. Macromolecules 2012, 45:3298-3311.
6. Carta M., Malpass-Evans R., Croad M., Rogan Y., Jansen J.C., Bernardo P., Bazzarelli F., McKeown N.B. An efficient polymer molecular sieve for membrane gas separations. Science 2013, 339:303-307.
7. Guiver M.D., Lee Y.M. Polymer rigidity improves microporous membranes. Science 2013, 339:284-285.
8. Li F.Y., Xiao Y., Ong Y.K., Chung T.-S. UV-rearranged PIM-1 polymeric membranes for advanced hydrogen purification and production. Adv. Energy Mater. 2012, 2:1456-1466.
9. 2 separation membranes. J. Membr. Sci. 2013, 428:260-266.
10. Armstrong S., Freeman B., Hiltner A., Baer E. Gas permeability of melt-processed poly(ether block amide) copolymers and the effects of orientation. Polymer 2012, 53:1383-1392.
11. Calle M., Lozano A.E., de Abajo J., de la Campa J.G., Álvarez C. Design of gas separation membranes derived of rigid aromatic polyimides. 1. Polymers from diamines containing di-tert-butyl side groups. J. Membr. Sci. 2010, 365:145-153.
12. Calle M., Lozano A.n.E., de La Campa J.G., de Abajo J. Novel aromatic polyimides derived from 5'-t-butyl-2'-pivaloylimino-3,4,3″,4″-m-terphenyltetracarboxylic dianhydride with potential application on gas separation processes. Macromolecules 2010, 43:2268-2275.
13. Hu Y.C., Chen C.J., Yen H.J., Lin K.Y., Yeh J.M., Chen W.C., Liou G.S Novel triphenylamine-containing ambipolar polyimides with pendant anthraquinone moiety for polymeric memory device, electrochromic and gas separation applications. J. Mater. Chem. 2013, 22:20394-20402.
14. Tena A., Lozano A.E., Palacio L., Marcos-Fernández A., Prádanos P., de Abajo J., Hernández A. Gas separation properties of systems with different amounts of long poly(ethylene oxide) segments for mixtures including carbon dioxide. Int. J. Greenhouse Gas Control 2013, 12:146-154.
15. Kardash I.Y., Ardashnikov A.Y., Yakubovich V.S., Braz G.I., Yakubpvich A.Y., Pravednikov A.N. The kinetics of thermal cyclodehydration of aromatic poly-o-hydroxyamides to polybenzoxazoles. Polym. Sci. U.S.S.R. 1967, 9:2160-2166.
16. Likhatchev D., Gutierrez-Wing C., Kardash I., Vera-Graziano R. Soluble aromatic polyimides based on 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane: synthesis and properties. J. Appl. Polym. Sci. 1996, 59:725-735.
17. Tullos G., Mathias L. Unexpected thermal conversion of hydroxy-containing polyimides to polybenzoxazoles. Polymer 1999, 40:3463-3468.
18. Tullos G.L., Powers J.M., Jeskey S.J., Mathias L.J. Thermal conversion of hydroxy-containing imides to benzoxazoles: polymer and model compound study. Macromolecules 1999, 32:3598-3612.
19. Kim S., Jo H.J., Lee Y.M. Sorption and transport of small gas molecules in thermally rearranged (TR) polybenzoxazole membranes based on 2,2-bis(3-amino-4-hydroxyphenyl)-hexafluoropropane (bisAPAF) and 4,4'-hexafluoroisopropylidene diphthalic anhydride (6FDA). J. Membr. Sci. 2013, 441:1-8.
20. Park C.H., Tocci E., Lee Y.M., Drioli E. Thermal treatment effect on the structure and property change between hydroxy-containing polyimides (HPIs) and thermally rearranged polybenzoxazole (TR-PBO). J. Phys. Chem. B 2012, 116:12864-12877.
21. Li S., Jo H.J., Han S.H., Park C.H., Kim S., Budd P.M., Lee Y.M. Mechanically robust thermally rearranged (TR) polymer membranes with spirobisindane for gas separation. J. Membr. Sci. 2013, 434:137-147.
22. Guo R., Sanders D.F., Smith Z.P., Freeman B.D., Paul D.R., McGrath J.E. Synthesis and characterization of thermally rearranged (TR) polymers: influence of ortho-positioned functional groups of polyimide precursors on TR process and gas transport properties. J. Mater. Chem. A 2013, 1:262-272.
23. Calle M., Chan Y., Jo H.J., Lee Y.M. The relationship between the chemical structure and thermal conversion temperatures of thermally rearranged (TR) polymers. Polymer 2012, 53:2783-2791.
24. Calle M., Lozano A.E., Lee Y.M. Formation of thermally rearranged (TR) polybenzoxazoles: effect of synthesis routes and polymer form. Eur. Polym. J. 2012, 48:1313-1322.
25. Park H.B., Jung C.H., Lee Y.M., Hill A.J., Pas S.J., Mudie S.T., Van Wagner E., Freeman B.D., Cookson D.J. Polymers with cavities tuned for fast selective transport of small molecules and ions. Science 2007, 318:254-258.
26. 2 separation. J. Membr. Sci. 2010, 359:11-24.
27. Calle M., Lee Y.M. Thermally rearranged (TR) poly(ether-benzoxazole) membranes for gas separation. Macromolecules 2011, 44:1156-1165.
28. Sanders D.F., Smith Z.P., Ribeiro C.P., Guo R., McGrath J.E., Paul D.R., Freeman B.D. Gas permeability, diffusivity, and free volume of thermally rearranged polymers based on 3,3'-dihydroxy-4,4'-diamino-biphenyl (HAB) and 2,2'-bis-(3,4-dicarboxyphenyl) hexafluoropropane dianhydride (6FDA). J. Membr. Sci. 2012, 409-410:232-241.
29. Muñoz D.M., Calle M., de la Campa J.G., de Abajo J., Lozano A.E. An improved method for preparing very high molecular weight polyimides. Macromolecules 2009, 42:5892-5894.
30. Han S.H., Misdan N., Kim S., Doherty C.M., Hill A.J., Lee Y.M. Thermally rearranged (TR) polybenzoxazole: effects of diverse imidization routes on physical properties and gas transport behaviors. Macromolecules 2010, 43:7657-7667.
31. Dewar M.J.S., Zoebisch E.G., Healy E.F., Stewart J.J.P. Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 1985, 107:3902-3909.
32. HyperChem(TM) Professional 8.0.3, Hypercube, Inc., 1115 NW 4th Street, Gainesville, Florida 32601, USA.
33. Xu Y., Fei F., Zhao J., Yu X. Preparation and characterization of novel polyimides with hydroxyl groups. J. Macromol. Sci., Phys. 2011, 50:2090-2102.
34. Ding M. Isomeric polyimides. Prog. Polym. Sci. 2007, 32:623-668.
35. Lozano A.E., De La Campa J.G., De Abajo J. Aromatic polyamides and polyimides derived from 3,3'-diaminobiphenyl: synthesis, characterization, and molecular simulation study. J. Polym. Sci., Part A: Polym. Chem. 1999, 37:4646-4655.
36. Comer A.C., Ribeiro C.P., Freeman B.D., Kalakkunnath S., Kalika D.S. Dynamic relaxation characteristics of thermally rearranged aromatic polyimides. Polymer 2013, 54:891-900.
37. Coleman M.R., Koros W.J. Isomeric polyimides based on fluorinated dianhydrides and diamines for gas separation applications. J. Membr. Sci. 1990, 50:285-297.
38. Han K., You K., Jang W.-H., Rhee T.H. Synthesis and properties of chlorinated polyimides. Macromol. Chem. Phys. 2000, 201:747-751.
39. Song G., Wang D., Zhao X., Dang G., Zhou H., Chen C. Synthesis and properties of polyimides-containing benzoxazole units in the main chain. High Perform. Polym. 2012, 25:354-360.
40. Okabe T., Morikawa A. Synthesis of polyimides from 3,3'-dihydroxybenzidine and conversion to polybenzoxazoles. High Perform. Polym. 2008, 20:53-66.
41. de Abajo J., de la Campa J.G., Lozano A.E. Designing aromatic polyamides and polyimides for gas separation membranes. Macromol. Symp. 2003, 199:293-306.
42. Budd P.M., McKeown N.B., Ghanem B.S., Msayib K.J., Fritsch D., Starannikova L., Belov N., Sanfirova O., Yampolskii Y., Shantarovich V. Gas permeation parameters and other physicochemical properties of a polymer of intrinsic microporosity: polybenzodioxane PIM-1. J. Membr. Sci. 2008, 325:851-860.
43. Budd P.M., Msayib K.J., Tattershall C.E., Ghanem B.S., Reynolds K.J., McKeown N.B., Fritsch D. Gas separation membranes from polymers of intrinsic microporosity. J. Membr. Sci. 2005, 251:263-269.
44. 2 gas separation membranes. J. Membr. Sci. 2010, 352:126-135.
45. Robeson L.M. Correlation of separation factor versus permeability for polymeric membranes. J. Membr. Sci. 1991, 62:165-185.
46. Robeson L.M. The upper bound revisited. J. Membr. Sci. 2008, 320:390-400.