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Synthesis and characterization of soluble aromatic azopolyamides containing sulfone and ether units

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Abstract

A series of new polyamides 3a–d containing aryl-azo, ether and sulfone groups in the main chain were synthesized from bis[4-(4-aminophenoxy)phenyl sulfone] 1 and several azo aromatic diacyl chlorides 2a–d by the low temperature solution polycondensation technique. FTIR spectroscopy, nuclear magnetic resonance (NMR) and elemental analyses confirmed the structure of these polymers. Owing to the aryl and amide groups in the main chain, these polymers exhibit photochromic properties as well as excellent thermal stabilities. The transition temperatures (T g) are between 242 and 265 °C, and the char yields at 800 °C in nitrogen atmosphere were above 39%. Based on incorporation of flexible ether linkages and polar sulfone groups, the polyamides show desirable solubility in organic solvents such as DMAc, N,N-dimethylformamide (DMF), N-methyl-2-pyrroidinone (NMP) and dimethylsulfoxide (DMSO). And it is exemplified that polyamide containing 2 and 2′ substitutes performed better solubility.

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References

  1. Ballauff M, Günter F S. Rigid Rod Polymers with Flexible Side Chains, 2. Observation of a Novel Type of Layered Mesophase[J]. Makromol. Chem. Rapid. Commun., 1987,8(2):93–97

    Article  CAS  Google Scholar 

  2. Steuer M, Hörth M, Ballauff M. Rigid Rod Polymers with Flexible Side Chains. X: Thermotropic Mesophases from Aromatic Stiff-chain Polyamides Bearing n-alkoxy Side Chains[J]. J. Polym. Sci., Part A: Polym. Chem., 1993,31(6):1609–1619

    Article  CAS  Google Scholar 

  3. Liou G S, Hsiao S H, Chen W C, Yen H J. A New Class of High T g and Organosoluble Aromatic Poly(amine-1,3,4-oxadiazole)s Containing Donor and Acceptor Moieties for Blue-Light-Emitting Materials [J]. Macromolecules 2006, 39(18):6036–6045

    Article  ADS  CAS  Google Scholar 

  4. Masatoshi K, Toshihiko M, Toshikazu K. Soluble Polyimides with Polyalicyclic Structure. 3. Polyimides from (4arH, 8acH) -Decahydro- lt, 4t: 5c, 8c-dimethanonaphthalene-2t,3t, 6c, 7c-tetracarboxylic 2, 3:6, 7-Dianhydride[J]. Macromolecules, 1994, 27(5):1117–1123

    Article  Google Scholar 

  5. Liaw D J, Liaw B Y, Yang C M. Synthesis and Properties of New Polyamides Based on bis[4-(4-aminophenoxy)phenyl] diphenylmethane[J]. Macromolecules, 1999,32(21):7248–7250

    Article  ADS  CAS  Google Scholar 

  6. Frank P G, Rolf M. Syntheses and Properties of Soluble Poly(arylene thioetherimide)s and the Corresponding Poly(arylene sulfone imide)s[J]. Polym. Bull., 1993,31(2):137–143

    Article  Google Scholar 

  7. Fitch J W, Reddy V S, Youngman P W, et al. Polyether Ketones Derived from bis[4-(4-fluorobenzoyl)phenyl] phenylphosphine Oxide[J]. Polymer, 2000, 41:2301–2304

    Article  CAS  Google Scholar 

  8. Liu B J, Wang G B, Hu W, Jin Y H, et al. Poly(aryl ether ketone)s with (3-methyl)phenyl and (3-trifluoromethyl) phenyl side groups[J]. J. Polym. Sci. Part A: Polym. Chem., 2002, 40(20): 3392–3398

    Article  CAS  Google Scholar 

  9. Zhu Q M, Dong L J, Niu Y S, Xiong C X, et al. Synthesis and Characterization of Novel Fluorinated Azopolyamides[J]. Polym. Bull., 2008, 61:569–580

    Article  CAS  Google Scholar 

  10. Fuming L, Jason J G, Paul S H, Shane F, et al. Dianhydride Architectural Effects on the Relaxation Behaviors and Thermal and Optical Properties of Organo-soluble Aromatic Polyimide Films[J]. Polymer, 1999, 40:4987–5002

    Article  Google Scholar 

  11. Kim K H, Jang S, Harris F W. Synthesis and Characterization of Photosensitive Polyimides for Optical Applications[J]. Macromolecules, 2001, 34(26):8925–8933

    Article  ADS  CAS  Google Scholar 

  12. Fang J H, Guo X X, Harada S, Watari T, et al. Novel Sulfonated Polyimides as Polyelectrolytes for Fuel Cell Application. 1. Synthesis, Proton Conductivity, and Water Stability of Polyimides from 4,4¢-Diaminodiphenyl Ether-2, 2¢-disulfonic Acid[J]. Macromolecules 2002, 35(24): 9022–9028

    Article  ADS  CAS  Google Scholar 

  13. Liaw D J, Liaw B Y, Jeng M Q. Synthesis and Properties of New Polyamides and Polyimides Derived from 2, 2′ - dimethyl - 4, 4′ - bis(4 - aminophenoxy) biphenyl[J]. Polymer, 1998, 39(8):1597–1607.

    Article  CAS  Google Scholar 

  14. Bellomo M R, Dipasquale G, Larosa A, et al. New Aromatic Polyamide Materials Containing Sulfone, Ether and Ketone Linkages[J]. Polymer, 1996, 37(13):2877–2881

    Article  CAS  Google Scholar 

  15. Xiong C X, Niu Y S, Zhou W, Dong L J. Synthesis of Azo Aromatic Diacyl Chlorides from Nitro Aromatic Acids[J]. J. Chem. Res., 2006, 139–140.

  16. Zhao Z H, Sun H Z, Sun M K. Determining the Intrinsic Viscosity of Carboxymethy Chitosan by One-point Method[J]. Marne Fisher Ies Research, (Chinese), 2002, 23(3):41–43

    MathSciNet  Google Scholar 

  17. Balasubramanian M, Nanjan M J, Santappa M. Synthesis, Characterization, and Fiber Studies of Certain Aromatic Polyamides[J]. Makromol. Chem.,1981, 182(3):853–859

    Article  CAS  Google Scholar 

  18. Domenico A, Eugenio A, Valeria B, Simona C, et al. Synthesis and Characterization of Segmented Liquid Crystalline Polymers with the Azo Group in the Main Chain[J]. Macromolecules 2004, 37(17):6418–6423

    Article  Google Scholar 

  19. Refah F A, Mona M F, Nadia A M. Thermal Stability and Degradation Behavior of Novel Wholly Aromatic Azopolyamide-hydrazides[J]. Polym. Degrad. Stab., 2006, 91:1530–1544

    Article  Google Scholar 

  20. Everlof G J, Jaycox G D. Stimuli-responsive Polymers. 4. Photo- and Thermo-regulated Chiroptical Behavior in Azobenzene-modified Polymers Fitted with Main Chain Spirobiindane Turns and Chiral Binaphthyl Bends[J]. Polymer, 2000, 41:6527–6536

    Article  CAS  Google Scholar 

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Correspondence to Chuanxi Xiong  (熊传溪).

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Funded by the National Natural Science Foundation of China (No. 50572081)

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Dong, L., Liu, L., Niu, Y. et al. Synthesis and characterization of soluble aromatic azopolyamides containing sulfone and ether units. J. Wuhan Univ. Technol.-Mat. Sci. Edit. 24, 594–598 (2009). https://doi.org/10.1007/s11595-009-4594-7

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  • DOI: https://doi.org/10.1007/s11595-009-4594-7

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