Skip to main content
Top
Published in: Journal of Polymer Research 7/2020

01-07-2020 | ORIGINAL PAPER

Study on the effect of different amounts of hydroxyl and tert-butyl substituted triphenylpyridine units on the properties of polyimide

Authors: Chengyun Yuan, Zhen Sun, Yinghan Wang

Published in: Journal of Polymer Research | Issue 7/2020

Log in

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

Four triphenylpyridine diamines with different substituent structure were successfully synthesized and polymerized to obtained polyimides (PIs) via one-step. The diamines and PIs were characterized by FTIR and 1H-NMR spectra. The aggregated structure of PIs was amorphous by wide angle X-ray diffraction test. The structure of the substituent had an important influence on the properties of PI (such as solubility, thermal stability, optical and mechanical properties). The introduction of tert-butyl group could reduce the solubility in non-polar solvent of PI. In addition, the introduction of hydroxyl group alone could increase the solubility in polar solvent of polymer due to the large polarity of the hydroxyl groups. All PIs exhibited high thermal stability and heat resistance, but the introduction of too much tert-butyl group reduced the thermal stability of PI. The introduction of tert-butyl group could effectively improve the optical properties of PIs. The maximum transmittance of PIs was above 85% (87.2–90.3%).

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literature
1.
go back to reference Yang Y, Lu H, Liu J, Shen Y (2018) Synthesis and binary/ternary write-once read-many-times electrical memory behaviors of carbazole-based polyimides bearing flexible linkage segment. Eur Polym J 108:10–19CrossRef Yang Y, Lu H, Liu J, Shen Y (2018) Synthesis and binary/ternary write-once read-many-times electrical memory behaviors of carbazole-based polyimides bearing flexible linkage segment. Eur Polym J 108:10–19CrossRef
2.
go back to reference Yang Y, Xia J, Ding Z, Zheng Y, Ding S, Shen Y (2018) Synthesis and resistive switching characteristics of polyimides derived from 2,7-aryl substituents tetraphenyl fluorene diamines. Eur Polym J 108:85–97CrossRef Yang Y, Xia J, Ding Z, Zheng Y, Ding S, Shen Y (2018) Synthesis and resistive switching characteristics of polyimides derived from 2,7-aryl substituents tetraphenyl fluorene diamines. Eur Polym J 108:85–97CrossRef
3.
go back to reference Park C-Y, Kim E-H, Kim JH, Lee YM, Kim J-H (2018) Novel semi-alicyclic polyimide membranes: synthesis, characterization, and gas separation properties. Polymer 151:325–333CrossRef Park C-Y, Kim E-H, Kim JH, Lee YM, Kim J-H (2018) Novel semi-alicyclic polyimide membranes: synthesis, characterization, and gas separation properties. Polymer 151:325–333CrossRef
4.
go back to reference Rehman W, Liaqat K, Fazil S, Saeed S, Waseem M, Shakeel M, Mir S, Bibi I, Guo C-Y (2019) Chemically tethered functionalized graphene oxide based novel sulfonated polyimide composite for polymer electrolyte membrane. J Polym Res 26:82CrossRef Rehman W, Liaqat K, Fazil S, Saeed S, Waseem M, Shakeel M, Mir S, Bibi I, Guo C-Y (2019) Chemically tethered functionalized graphene oxide based novel sulfonated polyimide composite for polymer electrolyte membrane. J Polym Res 26:82CrossRef
5.
go back to reference Wang N, Chen Y, Ren J, Huang X, Chen X, Li G, Liu D (2017) Electrically conductive polyaniline/polyimide microfiber membrane prepared via a combination of solution blowing and subsequent in situ polymerization growth. J Polym Res 24:42CrossRef Wang N, Chen Y, Ren J, Huang X, Chen X, Li G, Liu D (2017) Electrically conductive polyaniline/polyimide microfiber membrane prepared via a combination of solution blowing and subsequent in situ polymerization growth. J Polym Res 24:42CrossRef
6.
go back to reference Ignat M, Ovezea D, Hamciuc E, Hamciuc C, Dimitrov L (2014) Study on the electromechanical properties of polyimide composites containing TiO 2 nanotubes and carbon nanotubes. J Polym Res 21:536CrossRef Ignat M, Ovezea D, Hamciuc E, Hamciuc C, Dimitrov L (2014) Study on the electromechanical properties of polyimide composites containing TiO 2 nanotubes and carbon nanotubes. J Polym Res 21:536CrossRef
7.
go back to reference Wang Z, Li S, Wang J, Han E, Tian G, Wu D (2020) Dielectric and mechanical properties of polyimide fiber reinforced cyanate ester resin composites with varying resin contents. J Polym Res 27:160CrossRef Wang Z, Li S, Wang J, Han E, Tian G, Wu D (2020) Dielectric and mechanical properties of polyimide fiber reinforced cyanate ester resin composites with varying resin contents. J Polym Res 27:160CrossRef
8.
go back to reference Koolivand H, Sharif A, Kashani M-R, Karimi M, Salooki M-K, Semsarzadeh M-A (2014) Functionalized graphene oxide/polyimide nanocomposites as highly CO2-selective membranes. J Polym Res 21:599CrossRef Koolivand H, Sharif A, Kashani M-R, Karimi M, Salooki M-K, Semsarzadeh M-A (2014) Functionalized graphene oxide/polyimide nanocomposites as highly CO2-selective membranes. J Polym Res 21:599CrossRef
9.
go back to reference Wang Y-W, Chen W-C (2011) New photosensitive colorless polyimide-silica hybrid optical materials: synthesis, properties and patterning. Mater Chem Phys 126:24–30CrossRef Wang Y-W, Chen W-C (2011) New photosensitive colorless polyimide-silica hybrid optical materials: synthesis, properties and patterning. Mater Chem Phys 126:24–30CrossRef
10.
go back to reference Sun Z, Qin A, Chen Z, Wang Y (2010) Large pretilt angle induced by an anhydride-terminal hyperbranched polyimide liquid crystal alignment layer. Liq Cryst 37(3):345–348CrossRef Sun Z, Qin A, Chen Z, Wang Y (2010) Large pretilt angle induced by an anhydride-terminal hyperbranched polyimide liquid crystal alignment layer. Liq Cryst 37(3):345–348CrossRef
11.
go back to reference Okulska-Bozek M, Prot T, Borycki J, Kedzierski J (2006) Preparation and evaluation of polyimide layers as materials for nematic liquid crystal orientation. Liq Cryst 20(3):349–359CrossRef Okulska-Bozek M, Prot T, Borycki J, Kedzierski J (2006) Preparation and evaluation of polyimide layers as materials for nematic liquid crystal orientation. Liq Cryst 20(3):349–359CrossRef
12.
go back to reference Ghosh A, Sen SK, Banerjee S, Voit B (2012) Solubility improvements in aromatic polyimides by macromolecular engineering. RSC Adv 2:5900–5926CrossRef Ghosh A, Sen SK, Banerjee S, Voit B (2012) Solubility improvements in aromatic polyimides by macromolecular engineering. RSC Adv 2:5900–5926CrossRef
13.
go back to reference Chern Y-T, Twu J-T, Chen J-C (2009) High Tg and high organosolubility of novel polyimides containing twisted structures derived from 4-(4-amino-2-chlorophenyl)-1-(4-aminophenoxy)-2,6-di-tert-butylbenzene. Eur Polym J 45(4):1127–1138CrossRef Chern Y-T, Twu J-T, Chen J-C (2009) High Tg and high organosolubility of novel polyimides containing twisted structures derived from 4-(4-amino-2-chlorophenyl)-1-(4-aminophenoxy)-2,6-di-tert-butylbenzene. Eur Polym J 45(4):1127–1138CrossRef
14.
go back to reference Liu Y, Zhang Y, Guan S, Li L, Jiang Z (2008) Synthesis and properties of soluble fluorinated poly(ether imide)s with different pendant groups. Polymer 49(25):5439–5445CrossRef Liu Y, Zhang Y, Guan S, Li L, Jiang Z (2008) Synthesis and properties of soluble fluorinated poly(ether imide)s with different pendant groups. Polymer 49(25):5439–5445CrossRef
15.
go back to reference Lu Y, Wu Y, Xiao G, Dong Y, Zhao H, Hu Z (2014) Synthesis and characterization of poly(pyridine–imide)s with tert-butyl substituents. Adv Polym Sci 26(5):561–568 Lu Y, Wu Y, Xiao G, Dong Y, Zhao H, Hu Z (2014) Synthesis and characterization of poly(pyridine–imide)s with tert-butyl substituents. Adv Polym Sci 26(5):561–568
16.
go back to reference Gu Y, Sun Z, Gong S, Zhang H, Gong Q, Liu L, Wang Y (2015) Synthesis and characterization of soluble and thermally stable triphenylpyridine-containing aromatic polyimides. J Mater Sci 50:6552–6558CrossRef Gu Y, Sun Z, Gong S, Zhang H, Gong Q, Liu L, Wang Y (2015) Synthesis and characterization of soluble and thermally stable triphenylpyridine-containing aromatic polyimides. J Mater Sci 50:6552–6558CrossRef
17.
go back to reference Sun Z, Liu M, Yi L, Wang Y (2013) High glass transition of organo-soluble copolyimides derived from a rigid diamine with tert-butyl-substituted triphenylpyridine moiety. RSC Adv 3:7271CrossRef Sun Z, Liu M, Yi L, Wang Y (2013) High glass transition of organo-soluble copolyimides derived from a rigid diamine with tert-butyl-substituted triphenylpyridine moiety. RSC Adv 3:7271CrossRef
18.
go back to reference Zamidi Ahmad M, Navarro M, Lhotka M, Zornoza B, Téllez C, Fila V, Coronas J (2018) Enhancement of CO2/CH4 separation performances of 6FDA-based CO-polyimides mixed matrix membranes embedded with UiO-66 nanoparticles. Sep Purif Technol 192:465–474CrossRef Zamidi Ahmad M, Navarro M, Lhotka M, Zornoza B, Téllez C, Fila V, Coronas J (2018) Enhancement of CO2/CH4 separation performances of 6FDA-based CO-polyimides mixed matrix membranes embedded with UiO-66 nanoparticles. Sep Purif Technol 192:465–474CrossRef
19.
go back to reference C-P YANG, R-S CHEN, K-H CHEN (2003) Effects of Diamines and their fluorinated groups on the color lightness and preparation of Organosoluble aromatic polyimides from 2,2-Bis[4-(4-amino-2- trifluoromethylphenoxy)phenyl]-hexafluoropropane. J Polym Sci Pol Chem 41(7):922–938CrossRef C-P YANG, R-S CHEN, K-H CHEN (2003) Effects of Diamines and their fluorinated groups on the color lightness and preparation of Organosoluble aromatic polyimides from 2,2-Bis[4-(4-amino-2- trifluoromethylphenoxy)phenyl]-hexafluoropropane. J Polym Sci Pol Chem 41(7):922–938CrossRef
20.
go back to reference Li Y, Xu H, Tao X, Qian K, Fu S, Shen Y, Ding S (2011) Synthesis and memory characteristics of highly organo-soluble polyimides bearing a noncoplanar twisted biphenyl unit containing aromatic side-chain groups. J Mater Chem 21:1810–1821CrossRef Li Y, Xu H, Tao X, Qian K, Fu S, Shen Y, Ding S (2011) Synthesis and memory characteristics of highly organo-soluble polyimides bearing a noncoplanar twisted biphenyl unit containing aromatic side-chain groups. J Mater Chem 21:1810–1821CrossRef
21.
go back to reference Yan S, Chen W, Yang X, Chen C, Huang M, Xu Z, Yeung KWK, Yi C (2010) Soluble polyimides based on a novel pyridine-containing diamine m,p-PAPP and various aromatic dianhydrides. Polym Bull 66:1191–1206CrossRef Yan S, Chen W, Yang X, Chen C, Huang M, Xu Z, Yeung KWK, Yi C (2010) Soluble polyimides based on a novel pyridine-containing diamine m,p-PAPP and various aromatic dianhydrides. Polym Bull 66:1191–1206CrossRef
22.
go back to reference Chern Y-T, Tsai J-Y (2008) Low dielectric constant and high Organosolubility of novel polyimide derived from Unsymmetric 1,4-Bis(4-aminophenoxy)-2,6-di-tert-butylbenzene. Macromolecules 41:9556–9564CrossRef Chern Y-T, Tsai J-Y (2008) Low dielectric constant and high Organosolubility of novel polyimide derived from Unsymmetric 1,4-Bis(4-aminophenoxy)-2,6-di-tert-butylbenzene. Macromolecules 41:9556–9564CrossRef
23.
go back to reference Chern Y-T, Ju M-H (2009) Conformation of polyimide backbone structures for determination of the Pretilt angle of liquid crystals. Macromolecules 42:169–179CrossRef Chern Y-T, Ju M-H (2009) Conformation of polyimide backbone structures for determination of the Pretilt angle of liquid crystals. Macromolecules 42:169–179CrossRef
24.
go back to reference Huang W, Yan D, Lu Q (2001) Synthesis and characterization of a highly soluble aromatic polyimide from 4,49-Methylenebis(2-tertbutylaniline). Macromol Rapid Commun 22:1481–1484CrossRef Huang W, Yan D, Lu Q (2001) Synthesis and characterization of a highly soluble aromatic polyimide from 4,49-Methylenebis(2-tertbutylaniline). Macromol Rapid Commun 22:1481–1484CrossRef
Metadata
Title
Study on the effect of different amounts of hydroxyl and tert-butyl substituted triphenylpyridine units on the properties of polyimide
Authors
Chengyun Yuan
Zhen Sun
Yinghan Wang
Publication date
01-07-2020
Publisher
Springer Netherlands
Published in
Journal of Polymer Research / Issue 7/2020
Print ISSN: 1022-9760
Electronic ISSN: 1572-8935
DOI
https://doi.org/10.1007/s10965-020-02175-5

Other articles of this Issue 7/2020

Journal of Polymer Research 7/2020 Go to the issue

Premium Partners