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Synthesis, characterization, and structure-property relationships of aromatic polyimides containing 4,4′-diaminotriphenylmethane

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Abstract

This work reports two series of structurally different aromatic polyimides based on 4,4´-diaminodiphenylmethane (DPM) and 4,4´-diaminotriphenylmethane (TPM) and three commercial dianhydrides. All TPM-based polyimides formed membranes due to their high molecular weight (inherent viscosities ~0.93–1.14 dl/g), they exhibited high thermal stability (5 %: 490–544 °C), glass transition temperatures between 269 and 293 °C, and reasonable mechanical properties. The incorporation of pendant phenyl moieties in the TPM-based polyimides has a strong effect producing an improvement in solubility, thermal stability, density and gas permeability coefficient in comparison with DPM-based polyimides. The most interesting polyimide TPM-6FDA, containing phenyl and trifluoromethyl as bulky pendant groups, showed higher gas permeability coefficient for CO2 (23.73 Barrer) and the best ideal selectivity to the gas pair CO2/CH4 (α = 28.93).

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References

  1. Liaw DJ, Wang KL, Huang YC, Lee KR, Lai JY, Ha CS (2012) Advanced polyimides materials: Synthesis, physical properties and applications. Prog Polym Sci 37:907–974

    Article  CAS  Google Scholar 

  2. Mittal V (2011) High performance polymers and engineering plastics. Wiley-Scrivener, New Jersey

    Book  Google Scholar 

  3. Ree M (2006) High performance polyimides for applications in microelectronics and flat panel displays. Macromol Res 14:1–33

    Article  CAS  Google Scholar 

  4. Ghosh A, Sen SK, Banerjee S, Voit B (2012) Solubility improvements in aromatic polyimides by macromolecular engineering. RSC Adv 2:5900–5926

    Article  CAS  Google Scholar 

  5. de Abajo J, de la Campa JG (1999) Processable aromatic polyimides. Adv Polym Sci 140:23–59

    Article  Google Scholar 

  6. Yao P, Gu J, Lei X, Sun W, Chen Y, Zhang Q (2014) Highly soluble and thermally stable copolyimides modified with trifluoromethyl and siloxane. J Appl Polym Sci 132:41713

    Google Scholar 

  7. Zhuo L, Kou K, Wang Y, Yao P, Wu G (2014) Synthesis of soluble and thermally stable polyimides with phthalimide as pendent group from pyridine-containing triamine. J Mater Sci 49:5141–5150

    Article  CAS  Google Scholar 

  8. Chen JC, Rajendran K, Chang YH, Huang SW, Chern YT (2011) Highly transparent and organosoluble polyimides derived from 2,2´-disubstituted-4,4´-oxydianilines. J Appl Polym Sci 120:3159–3170

    Article  CAS  Google Scholar 

  9. Yi L, Li C, Huang W, Yan D (2014) Soluble aromatic polyimides with high glass transition temperature from benzidine containing tert-butyl groups. J Polym Res 21:572–581

    Article  Google Scholar 

  10. Kin SD, Lee S, Heo J, Kim SY, Chung IS (2013) Soluble polyimides with trifluoromethyl pendent groups. Polymer 54:5648–5654

    Article  Google Scholar 

  11. Hou Y, Chen G, Pei X, Fang X (2012) Synthesis and characterization of novel optically transparent and organosoluble polyimides based on diamines containing cyclohexane moiety. J Polym Res 19:9955

    Article  Google Scholar 

  12. Chen G, Pei X, Liu J, Fang X (2013) Synthesis and properties of transparent polyimides derived from trans- and cis-1,4-bis(3,4-dicarboxyphenoxy)cyclohexane dianhydrides. J Polym Res 20:159

    Article  Google Scholar 

  13. Calle M, Lozano AE, de Abajo J, de la Campa JG, Álvarez C (2010) Design of gas separation membranes derived of rigid aromatic polyimides. 1. Polymers from diamines containing di-tert-butyl side groups. J Membr Sci 365:145–153

    Article  CAS  Google Scholar 

  14. Xiao Y, Low BT, Hosseine SS, Chung TS, Paul DR (2009) The strategies of molecular architecture and modification of polyimide-based membranes for CO2 removal from natural gas- A review. Prog Polym Sci 34:561–580

    Article  CAS  Google Scholar 

  15. Budd PM, McKeown NB, Fritsch D (2005) Free volume and intrinsic microporosity in polymers. J Mater Chem 15:1977–1986

    Article  CAS  Google Scholar 

  16. Nagel C, Gunther-Schade K, Fritsch D, Strunskus T, Faupel F (2002) Free volume and transport properties in highly selective polymer membranes. Macromolecules 35:2071–2077

    Article  CAS  Google Scholar 

  17. Thran A, Kroll G, Faupel F (1999) Correlation between fractional free volume and diffusivity of gas molecules in glassy polymers. J Polym Sci: Part B: Polym Phys 37:3344–3335

    Article  CAS  Google Scholar 

  18. Likhatchev D, Alexandrova L, Tlenkopatchev M, Martinez-Richa A, Vera-Graziano R (1996) One-step synthesis of aromatic polyimides based on 4,4′-diaminotriphenylmethane. J Appl Polym Sci 61:815–818

    Article  CAS  Google Scholar 

  19. Likhatchev D, Alexandrova L, Tlenkopatchev M, Vilar R, Vera-Graziano R (1995) Soluble aromatic polyimides and polyamides based on 4,4′-diaminotriphenylmethane. J Appl Polym Sci 57:37–44

    Article  CAS  Google Scholar 

  20. Liaw DJ, Hsu PN, Chen WH, Lin SL (2002) High glass transitions of new polyamides, polyimides, and poly(amide − imide)s containing a triphenylamine group: Synthesis and characterization. Macromolecules 35:4669–4676

    Article  CAS  Google Scholar 

  21. Liaw DJ, Liaw BY, Yang CM (1999) Synthesis and properties of new polyamides based on bis[4-(4-aminophenoxy)phenyl]diphenylmethane. Macromolecules 32:7248–7250

    Article  CAS  Google Scholar 

  22. Oishi Y, Ishida M, Kakimoto M, Imai Y, Kurosaki T (1992) Preparation and properties of novel soluble aromatic polyimides from 4,4′-diaminotriphenylamine and aromatic tetracarboxylic dianhydrides. J Polym Sci: Part A: Polym Chem 30:1027–1035

    Article  CAS  Google Scholar 

  23. Vasilenko NA, Akhmet’eva YI, Sviridov YB, Berendyayav VI, Rogozhkina YD, Alkayeva OF, Koshelev KK, Izyumnikov AL, Kotov BV (1991) Soluble polyimides based on 4,4′-diaminotriphenylamine. Synthesis, molecular mass characteristics and solution properties. Polym Sci U.S.S.R. 33:1439–1450

    Article  Google Scholar 

  24. Guzmán-Lucero D, Guzmán J, Likhatchev D, Martínez-Palou R (2005) Microwave-assisted synthesis of 4,4′-diaminotriphenylmethane. Tetrahedron Lett 46:1119–1122

    Article  Google Scholar 

  25. Koton MM, Romanova MS, Laius LA, Sazanov YN, Fjodorova GN (1980) Aromatic polyimides based on 4,4′-diaminodiphenylmethane and some of its derivates. J Appl Sci USSR 53:1591–1593

    CAS  Google Scholar 

  26. Ren L, Fu W, Luo Y, Lu H, Jia D, Shen J, Pang B, Ko TM (2004) Thermal degradation of the polyimides from 4,4′-(hexafluoroisopropylidene) diphthalic dianhydride and 4,4´-diaminodiphenylmethane. J Appl Polym Sci 91:2295–2301

    Article  CAS  Google Scholar 

  27. Loría-Bastarrachea MI, Aguilar-Vega M (2013) Membranes from rigid block hexafluoro copolyaramides: Effect of the block lengths on gas permeation and ideal separation factors. J Membr Sci 443:36–44

    Article  Google Scholar 

  28. Díaz K, Vargas J, Del Castillo LF, Tlenkopatchev MA, Aguilar-Vega M (2005) Polynorbornene dicarboximides with cyclic pendant groups: Synthesis and gas transport properties. Macromol Chem Phys 206:2316–2322

    Article  Google Scholar 

  29. Ayala D, Lozano AE, de Abajo J, de la Campa JG (1999) Synthesis and characterization of novel polyimides with bulky pendant groups. J Polym Sci: Part A: Polym Chem 37:805–814

    Article  CAS  Google Scholar 

  30. Kaneda T, Katsura T, Nakagawa K, Makino H, Horio M (1986) High-strength–high-modulus polyimide fibers II. Spinning and properties of fibers. J Appl Polym Sci 3:3151–3176

    Article  Google Scholar 

  31. Clair TLS (1990) In: Wilson D, Stenzenberger HD, Hergenrother PM (eds) Polyiimides. New York, Springer

    Google Scholar 

  32. Ragosta G, Abbate M, Musto P, Scarinzi G (2012) Effect of the chemical structure of aromatic polyimides on their thermal aging, relaxation behavior and mechanical properties. J Mater Sci 47:2637–2647

    Article  CAS  Google Scholar 

  33. Kothawade SS, Kulkarni MP, Kharul UK, Patil AS, Vernekar SP (2008) Synthesis, characterization, and gas permeability of aromatic polyimides containing pendant phenoxy group. J Appl Polym Sci 108:3881–3889

    Article  CAS  Google Scholar 

  34. Van Krevelen DW, Hoftyzer PJ (1972) Properties of Polymers. Correlation with Chemical Structure, Elsevier, New York

    Google Scholar 

  35. Pixton MR, Paul DR (1994) In: Paul DR, Yampol’skii YP (eds) Polymeric Gas Separation Membranes. Boca Raton, CRC press

    Google Scholar 

  36. Bandyopadhyay P, Bera D, Ghosh S, Banerjee S (2014) Synthesis, characterization and gas transport properties of cardobis(phenylphenyl)fluorine based on semifluorinated poly(ether amide)s. RSC Adv 4:28078–28092

    Article  CAS  Google Scholar 

  37. Ayala D, Lozano AE, de Abajo J, García-Pérez C, de la Campa JG, Peinemann KV, Freeman BD, Prabhakar R (2003) Gas separation properties of aromatic polyimides. J Membr Sci 215:61–73

    Article  CAS  Google Scholar 

  38. Robeson LM (2008) The upper bound revisited. J Membr Sci 320:390–400

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors acknowledge the financial support of Programa de Apoyo a Proyectos de Investigación e Innovación Tecnológica (PAPIIT) through Grant IT101114/26; moreover, the partial support from grant 127499 SENER-CONACyT is gratefully acknowledge. Additional thanks are expressed to M.D. Damaris Cabrero for her technical assistance in the thermal analysis.

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Authors and Affiliations

  1. Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior s/n, Ciudad Universitaria, 04510, México, D.F., México

    C. Aguilar-Lugo & L. Alexandrova

  2. Unidad de Materiales, Centro de Investigación Científica de Yucatán, A.C. Chuburna de Hidalgo, Calle 43 No.130, 97200, Mérida, Yucatán, México

    J. L. Santiago-García, M. I. Loría-Bastarrachea & M. Aguilar-Vega

  3. Gerencia de Transformación de la Biomasa, Instituto Mexicano del Petróleo, Eje Central L. Cárdenas 152, Col. San Bartolo Atepehuacan, 07730, México, D.F., México

    D. Guzmán-Lucero

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  1. C. Aguilar-Lugo
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  2. J. L. Santiago-García
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  3. M. I. Loría-Bastarrachea
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  4. D. Guzmán-Lucero
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  5. L. Alexandrova
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Correspondence to M. Aguilar-Vega.

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Aguilar-Lugo, C., Santiago-García, J.L., Loría-Bastarrachea, M.I. et al. Synthesis, characterization, and structure-property relationships of aromatic polyimides containing 4,4′-diaminotriphenylmethane. J Polym Res 23, 49 (2016). https://doi.org/10.1007/s10965-016-0939-z

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