Abstract
Novel polyimides containing furan moieties were prepared from the resulting furanic diamine monomers with various aromatic dianhydrides including 1,2,4,5-benzene-tetracarboxylic dianhydride, 3,3′,4,4′-biphenyltetracarboxylic dianhydride, 4,4′-oxydiphthalic anhydride, and hexafluoroisopropylidene 2,2-bis(phthalic anhydride), via a two-step process. The resulting polyimides were characterized by solubility tests, viscosity measurements, FTIR, 1H NMR spectroscopy, differential scanning calorimetric (DSC), and thermogravimetric analysis (TGA) analysis. The polyimides with inherent viscosities in the range of 0.048–0.095 L/g showed excellent solubility in aprotic amide and organic solvents, such as N,N-dimethylacetamide, N-methyl-2-pyrrolidinone, dimethylformamide and acetone, chloroform, etc. DSC showed glass transition temperatures (T g) in the range of 116–143 °C. These polymers showed excellent thermal stability up to 390 °C.
Similar content being viewed by others
References
Abajo J, Campa J G (1999) Processable aromatic polyimides. In: Progress in polyimide chemistry I. Advances in polymer science, vol 140. Springer, Berlin, pp 23–59
Stephen ZD, Zongquan W, Eashoo M, Hsu Steven LC, Harris Frank W (1991) A high-performance aromatic polyimide fibre: 1. Structure, properties and mechanical-history dependence. Polymer 32(10):1803–1810
Hergenrother PM, Havens SJ (1994) Polyimides containing quinoxaline and benzimidazole units. Macromolecules 27:4659–4664
Banihashemi A, Abdolmaleki A (2004) Novel aromatic polyimides derived from benzofuro[2,3-b]benzofuran-2,3,8,9-tetracarboxylic dianhydride (BBTDA). Eur Polym J 40:1629–1635
Kawakami H, Nakajima K, Shimizu H, Nagaoka S (2003) Gas permeation stability of asymmetric polyimide membrane with thin skin layer: effect of polyimide structure. J Membr Sci 212:195–203
Miyazaki E, Tagawa M, Yokota K, Yokota R, Kimoto Y, Ishizawa J (2010) Investigation into tolerance of polysiloxane-block-polyimide film against atomic oxygen. Acta Astronaut 66:922–928
Kuntman A, Kuntman H (2000) A study on dielectric properties of a new polyimide film suitable for interlayer dielectric material in microelectronics applications. Microelectron J 31(8):629–634
Akanksha S, Rao VL, Prabhakaran PV, Ninan KN (2003) Synthesis and characterization of polyamides and poly(amide-imide)s derived from 2,2-bis(4-aminophenoxy) benzonitrile. Eur Polym J 39(2):401–405
Ma SP, Takahashi T (1996) Binary blends of a new wholly aromatic thermoplastic polyimide and poly(ether-imide). Polymer 37(25):5589–5596
Fengchun Y, Yanfeng L, Qianqian B, Shujiang Z, Tao M, Jiujiang Z (2010) Characterizations and thermal stability of soluble polyimide derived from novel unsymmetrical diamine monomers. Polym Degrad Stab 95(9):1950–1958
Koning CE, Teuwen L, De Plaen A, Mercier JP (1996) Enhancement of the crystallinity of a thermoplastic polyimide. Polymer 37(25):5619–5625
Prashant S, Ravindra R, Manikrao M, Noormahamad N, Prakash P (2007) Synthesis of aromatic poly(amide-imide)s from novel diimide-diacid (DIDA) containing sulphone and bulky pendant groups by direct polycondensation with various diamines. Eur Polym J 43(12):5047–5054
Chun-Shan W, Tsu-Shang L (2000) Synthesis and characterization of polyimides containing naphthalene pendant group and flexible ether linkages. Polymer 41(10):3581–3591
Belgacem MN, Gandini A (eds) (2008) Monomers, polymers and composites from renewable resources. Elsevier, Amsterdam, pp 39–66
Abid S, El Gharbi R, Gandini A (2004) Polyamides incorporating furan moieties. 5. Synthesis and characterisation of furan-aromatic homologues. Polymer 45(17):5793–5801
Afli A, Abid S, El Gharbi R (2008) All furanic polyhydrazides and corresponding polyoxadiazoles. e-Polymer 64:1–8
Abid S, Matoussi S, El Gharbi R, Gandini A (2006) A preliminary study of polyureas and poly(parabanicacid)s incorporating furan rings. Polym Bull 57:43–50
Abid M, Kammoun W, El Gharbi R, Fradet A (2008) Copolyesters containing terephthalic and bio-based furanic units by melt-polycondensation. Macromol Mater Eng 293(1):39–44
Kammoun W, Salhi S, Abid S, Tessier M, El Gharbi R, Fradet A (2005) Synthesis, characterization and ring-closing depolymerization of furanic polyesters. e-Polymer 36:1–13
Abid S, El Gharbi R, Gandini A (2004) Polyamide-imides bearing furan moieties. 1. Solution polycondensation of aromatic dianhydrydes with 2-furoic acid dihydrazides. Polymer 45(19):6469–6478
Biolley N, Grégoire M, Pascal T, Sillion B (1991) Synthesis and characterization of a linear CARDO polyimide from (5,5′-bisisobenzofuran)-1,1′,3,3′-tetrone and 4,4′-(9H-fluoren-9-ylidene)bisphenylamine. Polymer 32(17):3256–3261
Pyo SM, Kim SI, Shin TJ, Park HK, Ree M, Park KH, Kang JS (1998) Synthesis and characterization of a new blue-light-emitting polyimide. Macromolecules 31(15):4777–4781
Pyo SM, Kim SI, Shin TJ, Ree M, Park KH, Kang JS (1999) Synthesis and blue light-emitting characteristic of rod-like poly(4,4′-biphenylene pyromellitimide) with furyl side groups. Polymer 40(1):125–130
Xiaolong W, Yanfeng L, Shujiang Z, Tao M, Yu S, Xin Z (2006) Synthesis and characterization of novel polyimides derived from pyridine-bridged aromatic dianhydride and various diamines. Eur Polym J 42(6):1229–1239
Shujiang Z, Yanfeng L, Daxue Y, Xiaolong W, Xin Z, Yu S, Shiyong Y (2005) Study on synthesis and characterization of novel polyimides derived from 2,6-Bis(3-aminobenzoyl) pyridine. Eur Polym J 41(5):1097–1107
Mallakpour S, Rafiemanzelat F (2005) Diisocyanate route as a convenient method for the preparation of novel optically active poly(amide–imide)s based on N-trimellitylimido-S-valine. Eur Polym J 41(12):2945–2955
Baozhong L, Tianbai H, Mengxian DM (1999) A comparative study of insoluble and soluble polyimide thin films. Polymer 40(3):789–794
Acknowledgment
The authors acknowledge the Ministry of Higher Education, Scientific Research and Technology in Tunisia for their financial support. They also thank Prof. Rachid El Gharbi for his useful discussions about this work.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Maktouf, L.B., Ghorbel, I., Afli, A. et al. Polyimides based on furanic diamines and aromatic dianhydrides: synthesis, characterization and properties. Polym. Bull. 67, 1111–1122 (2011). https://doi.org/10.1007/s00289-010-0441-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-010-0441-4