Abstract
Montmorillonite clay modified with the bio-active trifunctional l-tyrosine amino acid salt was used as a reactive organoclay (OC) for the preparation of poly(amide-imide) (PAI)/OC hybrid films. One of the functional groups of the l-tyrosine as the swelling agent formed an ionic bond with the negatively charged silicates, whereas the remaining functional groups were available for further reaction with polymer matrix. The soluble PAI with amine end groups including phenylalanine amino acid was synthesised under green condition using molten tetra-butylammonium bromide by direct polymerization reaction of chiral diacid and 2-(3,5-diaminophenyl)benzimidazole. PAI/OC bio-nanocomposites films containing different contents of OC were prepared via solution intercalation method through blending of OC with the PAI solution. X-ray diffraction and transmission electron microscopy revealed that the dispersion of silicate layers in the PAI created an exfoliated structure as a result of using the trifunctional groups of the swelling agent. The structure and thermal behavior of the synthesised materials were characterized by a range of methods, including X-ray diffraction, Fourier transform infrared spectroscopy, 1H-NMR, electron microscopy, elemental and thermogravimetric analysis techniques. Thermogravimetric analysis results indicated that the addition of OC into the PAI matrix was increased in the thermal decomposition temperatures of the resulted bio-nanocomposites.
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References
Abdalla MO, Dean D, Campbell S (2002) Viscoelastic and mechanical properties of thermoset PMR-type polyimide–clay nanocomposites. Polymer 43:5887–5893
Absalan G, Akhond M, Sheikhian L (2010) Partitioning of acidic, basic and neutral amino acids into imidazolium-based ionic liquids. Amino Acids 39:167–174
Ayala V, Maya EM, Garcia JM, De La Campa JG, Lozano AE, De Abajo J (2005) Synthesis, characterization, and water sorption properties of new aromatic polyamides containing benzimidazole and ethylene oxide moieties. J Polym Sci Part A Polym Chem 43:112–121
Chao TY, Chang HL, Su WC, Wu JY, Jeng RJ (2008) Nonlinear optical polyimide/montmorillonite nanocomposites consisting of azobenzene dyes. Dyes Pigm 77:515–524
Chen J, Zhou Y, Nan Q, Ye X, Sun Y, Zhang F, Wang Z (2007) Preparation and properties of optically active polyurethane/TiO2 nanocomposites derived from optically pure 1,10-binaphthyl. Eur Polym J 43:4151–4159
Chung IS, Park CE, Ree M, Kim SY (2001) Soluble polyimides containing benzimidazole rings for interlevel dielectrics. Chem Mater 13:2801–2806
Delozier DM, Orwoll RA, Cahoon JF, Ladislaw JS, Smith JG Jr, Connell JW (2003) Polyimide nanocomposites prepared from high-temperature, reduced charge organoclays. Polymer 44:2231–2241
Eversloh TL, Nicole C, Santos S, Stephanopoulos G (2007) Perspectives of biotechnological production of l-tyrosine and its applications. Appl Microbiol Biotechnol 77:751–762
Garlick PJ (2005) The role of leucine in the regulation of protein metabolism. J Nutr 135:1553S–1556S
Huang XS, Huang YG, Qing FL (2009) Novel poly(aryl ether)s containing benzimidazole pendants derived from 1,4-bis(2-benzimidazolyl)-2,5-difluorobenzene. J Mater Sci 44:3566–3573
Ishii J, Shimizu N, Ishihara N, Ikeda Y, Sensui N, Matano T, Hasegawa M (2010) Spontaneous molecular orientation of polyimides induced by thermal imidization (4): casting- and melt-induced in-plane orientation. Eur Polym J 46:69–80
Ivarez-Gallego YA, Pereira Nunes S, Lozano AE, de la Campa JG, de Abajo J (2007) Synthesis and properties of novel polyimides bearing sulfonated benzimidazole pendant groups. Macromol Rapid Commun 28:616–622
Karatas S, Kayaman-Apohan N, Demirer H, Gungor A (2007) Polyimide–silica hybrid coatings: morphological, mechanical, and thermal investigations. Polym Adv Technol 18:490–496
Koprowska-Ratajska M, Kluczyk A, Stefanowicz P, Bartosz-Bechowski H, Szewczuk Z (2009) Solid phase synthesis of peptides containing novel amino acids, substituted 3-benzimidazolealanines. Amino Acids 36:309–315
Koyam E, Sanda F, Endo T (1997) Syntheses and radical polymerizations of methacrylamides derived from optically active amino alcohols. Macromol Chem Phys 198:3699–3707
Lan T, Kaviratna PD, Pinnavaia TJ (1994) On the nature of polyimide–clay hybrid composites. Chem Mater 6:573–575
Li XR, Li YS (2003) Synthesis and characterization of hyperbranched aromatic poly(ester-imide)s. Polymer 44:3855–3863
Li XD, Zhong ZX, Han SH, Lee SH, Lee MH (2005) Facile modifications of polyimide via chloromethylation: II. Synthesis and characterization of thermocurable transparent polyimide having methylene acrylate side groups. Polym Int 54:406–411
Li Q, Yang X, Chen W, Yi C, Xu Z (2008) Preparation of poly(amic acid) and polyimide via microwave-assisted polycondensation of aromatic dianhydrides and diamines. Macromol Symp 261:148–156
Liang ZM, Yin J, Xu HJ (2003) Polyimide/montmorillonite nanocomposites based on thermally stable, rigid-rod aromatic amine modifiers. Polymer 44:1391–1399
Lina B, Liua H, Zhanga S, Yuan C (2004) Structure and infrared emissivity of silicon-containing polyimide/BaTiO3 nanocomposite films. J Solid State Chem 177:3849–3852
Ma X, Lee NH, Oh HJ, Hwang JS, Kim SJ (2010) Preparation and characterization of silica/polyamide-imide nanocomposite thin films. Nanoscale Res Lett 5:1846–1851
Mallakpour S, Dinari M (2011a) Progress in synthetic polymers based on natural amino acids. J Macromol Sci Part A Pure Appl Chem 48:644–679
Mallakpour S, Dinari M (2011b) Insertion of novel optically active poly(amide-imide) chains containing pyromellitoyl-bis-l-phenylalanine linkages into the nanolayered silicates modified with l-tyrosine through solution intercalation. Polymer 52:2514–2523
Mallakpour S, Dinari M (2011c) Preparation and characterization of new organoclays using natural amino acids and Cloisite Na+. Appl Clay Sci 51:353–359
Mallakpour S, Dinari M (2012a) Chiral poly(amide-imide)/organoclay nanocomposites derived from pyromellitoyl-bis-l-isoleucine and benzimidazole containing diamine: synthesis, nanostructure, and properties. Colloid Polym Sci 290:81–90
Mallakpour S, Dinari M (2012b) Preparation, characterization, and thermal properties of organoclay hybrids based on trifunctional natural amino acids. Therm Anal Calorim. doi:10.1007/s10973-012-2375-6
Mallakpour S, Dinari M (2012c) Novel nanostructure amino acid-based poly(amide–imide)s enclosing benzimidazole pendant group in green medium: fabrication and characterization. Amino Acids 43:1605–1613
Mallakpour S, Khani M (2010) Construction of chiral polyesters from polycondensation of multifunctional monomer containing both flexible amino acid and rigid pendant groups with aromatic diols. Amino Acids 39:841–848
Mallakpour S, Asadi P, Sabzalian MR (2011) Synthesis of biodegradable chiral poly(ester-imide)s derived from valine, leucine and tyrosine-containing monomers. Amino Acids 41:1215–1222
Nguyen T, Wang X (2010) Multifunctional composite membrane based on a highly porous polyimide matrix for direct methanol fuel cells. J Power Sources 195:1024–1030
Palacio M, Bhushan B (2010) A review of ionic liquids for green molecular lubrication in nanotechnology. Tribol Lett 40:247–268
Samui AB, Ratna D, Chavan JG, Deb PC (2002) Modification of epoxy resin with optically active carboxylic acid. J Appl Polym Sci 86:2523–2529
Van Krevelen DW, Hoftyzer PJ (1976) Properties of polymers, 3rd edn. Elsevier scientific publishing, New York
Wang YC, Fan SC, Lee KR, Li CL, Huang SH, Tsai HA, Lai JY (2004) Polyamide/SDS–clay hybrid nanocomposite membrane application to water–ethanol mixture pervaporation separation. J Memb Sci 239:219–226
Wang L, Wang Y, Cao D (2009) Synthesis and characterization of novel biodegradable polyamides containing α-amino acid. J Macromol Sci Part A Pure Appl Chem 46:312–320
Xu J, Li RKY, Meng YZ, Mai YW (2006) Biodegradable poly(propylene carbonate)/montmorillonite nanocomposites prepared by direct melt intercalation. Mater Res Bull 41:244–252
Yeh JM, Hsieh CF, Jaw JH, Kuo TH, Huang HY, Lin CL, Hsu MY (2005) Organo-soluble polyimide (ODA–BSAA)/montmorillonite nanocomposite materials prepared by solution dispersion technique. J Appl Polym Sci 95:1082–1090
Yin M, Li C, Guan G, Yuan X, Zhang D, Xiao Y (2009) In situ synthesis of poly(ethylene terephthalate)/clay nanocomposites using TiO2/SiO2 sol-intercalated montmorillonite as polycondensation catalyst. Polym Eng Sci 49:1562–1572
Yu YH, Yeh JM, Liou SJ, Chang YP (2004) Organo-soluble polyimide (TBAPP–OPDA)/clay nanocomposite materials with advanced anticorrosive properties prepared from solution dispersion technique. Acta Mater 52:475–486
Yu YY, Chien WC, Tsai TW (2010) High transparent soluble polyimide/silica hybrid optical thin films. Polym Test 29:33–40
Zhai F, Guo X, Fang J, Xu H (2007) Synthesis and properties of novel sulfonated polyimide membranes for direct methanol fuel cell application. J Membr Sci 296:102–109
Zhao Y, Li M, Lu Q (2008) Tunable wettability of polyimide films based on electrostatic self-assembly of ionic liquids. Langmuir 24:3937–3943
Acknowledgments
The authors wish to sincerely thank the Research Affairs Division Isfahan University of Technology (IUT), Isfahan, for partial financial support. Further financial support from National Elite Foundation (NEF), Iran Nanotechnology Initiative Council (INIC) and Center of Excellency in Sensors and Green Chemistry Research (IUT) is gratefully acknowledged. We also thank Dr. H. Jalili for the English editing.
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Mallakpour, S., Dinari, M. Chiral bio-nanocomposites based on thermally stable poly(amide-imide) having phenylalanine linkages and reactive organoclay containing tyrosine amino acid. Amino Acids 44, 1021–1029 (2013). https://doi.org/10.1007/s00726-012-1436-2
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DOI: https://doi.org/10.1007/s00726-012-1436-2