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New organosoluble polyarylates containing pendent fluorene units: synthesis, characterization and thermal behaviour

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Abstract

The new pendent bisphenol containing flourene unit, 1,1-bis-[(4-hydroxyphenyl)-1-(9H-fluoren-2-yl)]ethane (BHPFE) are synthesized from commercially available 2-acetylfluorene and phenol and then utilized for the synthesis of three new kinds of polyarylates by phase-transfer catalyzed interfacial polycondensation technique with two different benzenedicarbonyl chlorides (isophthaloyl chloride (IPC) and terephthaloyl chloride (TPC)) and its mixture of 50:50 mol%. The synthesized BHPFE and polyarylates are well-characterized using FTIR, 1H-NMR, 13C-NMR, and GPC measurements. Results of these new polyarylates are compared with aromatic polyesters derived from Bisphenol-A with TPC as well as IPC. Inherent viscosities and number average molecular weights (Mn) of polyarylates are found in the range of 0.11–0.71 dl/g and 59,516–79,371 g/mol, respectively. Compared with the polyarylates synthesized from Bisphenol-A, the polyarylates synthesized from BHPFE monomers exhibited high solubility in various organic solvents like dichloromethane, tetrahydrofuran, chloroform, pyridine and N, N-dimethylformamide and could be easily solution-cast into transparent films. The WXRD study indicated that new polyarylates are amorphous in nature. Polyarylates showed the glass transition temperature (Tg) inbetween 123–151 °C and 10% weight loss (T10) ranging from 399°–447 °C under nitrogen atmosphere indicating their thermal stability. Polyarylates having tensile strength of 3.35 to 5.36 MPa with optical transparency cutoff in the wavelength of 309–326 nm range.

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References

  1. Vinogradova SV, Vasnev VA, Valetskii PM (1994) Polyarylates: synthesis and properties. Russ Chem Rev 63:833–851

    Article  Google Scholar 

  2. Cassidy PE (1980) Thermally stable polymers, synthesis and properties. Marcel Dekker, New York

    Google Scholar 

  3. Arroyo M (1997) Polyarylates. In: Olabisi O (ed) Handbook of thermoplastics. Marcel Dekker, New York, pp 599–608

    Google Scholar 

  4. Bhowmik PK, Han H (1993) Fully aromatic liquid crystalline polyesters of phenyl-substituted 4,4’-biphenols and l,l’-binaphthyl-4,4’-diol with either 2-bromoterephthalic acid or 2-phenylterephthalic acid. Macromolecules 26:5287–5294

    Article  CAS  Google Scholar 

  5. Bier G (1974) Polyarylates (polyesters from aromatic dicarboxylic acids and bisphenols). Polymer 15:527–535

    Article  CAS  Google Scholar 

  6. Morgan PW (1970) Aromatic polyesters with large cross-planar substituents. Macromolecules 3:536–544

    Article  CAS  Google Scholar 

  7. Jeong HJ, Kakimoto M, Imai Y (1991) Synthesis and characterization of novel polyarylates from 2,5-bis(4-hydroxyphenyl)-3,4-diphenylfuran and aromatic diacid chlorides. J Polym Sci A Polym Chem 29:1293–1299

    Article  CAS  Google Scholar 

  8. Hsiao SH, Chang HY (1995) Synthesis and properties of aromatic polyesters and brominated polyesters derived from α,α’-bis(4-hydroxyphenyl)-1,4(or1,3)-diisopropylbenzene. J Polym Res 2:99–108

    Article  CAS  Google Scholar 

  9. Liou GS, Chern YT (1999) Synthesis and properties of new polyarylates from 1,4-bis(4-carboxyphenoxy)naphthyl or 2,6-bis(4-carboxyphenoxy)naphthyl and various bisphenols. J Polym Sci A Polym Chem 37:645–652

    Article  CAS  Google Scholar 

  10. Chern YT, Huang CM (1998) Synthesis and characterization of new polyesters derived from 1,6- or 4,9-diamantanedicarboxylic acyl chlorides with aryl ether diols. Polymer 39:2325–2329

    Article  CAS  Google Scholar 

  11. Shan WC, Hsuan LC (1999) Synthesis and properties of phosphorus containing polyarylates derived from 2-(6-oxido-6H-dibenz‹c,e›‹1,2›oxaphosphorin-6-yl)-1,4-dihydroxy phenylene. Polymer 40:4387–4398

    Article  CAS  Google Scholar 

  12. Bucio E, Fitch JW, Venumbaka SR, Cassidy PE (2005) Synthesis and properties of aliphatic spirodilactam diphenol containing polyesters. Polymer 46:3971–3974

    Article  CAS  Google Scholar 

  13. Joshi MD, Sarkar A, Yemul OS, Wadgaonkar PP, Lonikar SV, Maldar NN (1997) Synthesis and characterization of silicon containing cardo polyesters. J Appl Polym Sci A 64:1329–1335

    Article  CAS  Google Scholar 

  14. Vibhute SS, Joshi MD, Wadgaonkar PP, Patil AS, Maldar NN (1997) Synthesis and characterization of new cardo polyesters. J Polym Sci A Polym Chem 35:3227–3234

    Article  CAS  Google Scholar 

  15. Watanabe S, Murayama H, Murata M, Tanabe M, Imai Y (1998) Synthesis and characterization of new aromatic polyesters and a polyether derived from 2,2-bis(4-hydroxyphenyl)-1,2-diphenylethanone. J Polym Sci A Polym Chem 36:2229–2235

    Article  CAS  Google Scholar 

  16. Kajiyama M, Kudo J, Mizumachi H (1999) Synthesis and characterization of aromatic polymers derived from 5-perfluoroalkylisophthalic acid. J Polym Sci A Polym Chem 37:1135–1144

    Article  CAS  Google Scholar 

  17. Liaw DJ, Liaw BY, Hsu JJ, Cheng YC (2000) Synthesis and characterization of new soluble polyesters derived from various cardo bisphenols by solution polycondensation. J Polym Sci A Polym Chem 38:4451–4456

    Article  CAS  Google Scholar 

  18. Loria-Bastarrachea MI, Vazquez-Torres H, Aguilar-Vega M (2002) Synthesis and characterization of aromatic polyesters and copolyesters from 4,4′-(1-hydroxyphenylidene)- diphenol and 4,4′-(9-fluorenylidene)diphenol. J Appl Polym Sci 86:2515–2522

    Article  CAS  Google Scholar 

  19. Bhole YS, Kharul UK (2003) Effect of fluorene-bisphenol ring substitution and bridge rigidity on physical and gas permeation properties of resulting polyarylates. Polym Int 52:1474–1479

    Article  CAS  Google Scholar 

  20. Hsiao SH, Chiang HW (2004) Synthesis and properties of new fluorinated polyarylates derived from 1,1-bis(4-hydroxyphenyl)-1-phenyl-2,2,2-trifluoroethane and aromatic diacid chlorides. Eur Polym J 40:1691–1697

    Article  CAS  Google Scholar 

  21. Tamami B, Yeganeh H, Ali KG (2004) Synthesis and characterization of novel polyesters derived from 4-aryl-2,6-bis(4-chlorocarbonyl phenyl) pyridines and various aromatic diols. Eur Polym J 40:1651–1657

    Article  CAS  Google Scholar 

  22. Hsiao SH, Chiang HW (2005) Synthesis and structure-property study of polyarylates derived from bisphenols with different connector groups. J Polym Res 12:211–218

    Article  CAS  Google Scholar 

  23. Honkhambe PN, Avadhani CV, Wadgaonkar PP, Salunkhe MM (2007) Synthesis and characterization of new aromatic polyesters containing biphenyl side groups. J Appl Polym Sci 106:3105–3110

    Article  CAS  Google Scholar 

  24. Liou GS, Hsiao SH, Huang HM, Chang CW, Yen HJ (2007) Synthesis and photophysical properties of novel organo-soluble polyarylates bearing triphenylamine moieties. J Polym Res 14:191–199

    Article  CAS  Google Scholar 

  25. Liou GS, Chang CW, Huang HM, Hsiao SH (2007) Synthesis and electrochromism of novel organosoluble polyarylates bearing triphenylamine moieties. J Polym Sci A Polym Chem 45:2004–2014

    Article  CAS  Google Scholar 

  26. Cardena-Vazquez MC, Aguilar-Vega M (2010) Synthesis and characterization of isophthalic polyesters and copolyesters based on 2,4-Dihydroxybenzophenone and 4,4’-(hexafluoroisopropylidene)diphenol. High Perform Polym 22:184–197

    Article  CAS  Google Scholar 

  27. Liou GS, Lin SM, Yen HG (2008) Synthesis and photoluminescence properties of novel polyarylates bearing pendent naphthylamine chromophores. Eur Polym J 44:2608–2618

    Article  CAS  Google Scholar 

  28. Honkhambe PN, Bhairamadgi NS, Biyani MV, Wadgaonkar PP, Salunkhe MM (2010) Synthesis and characterization of new aromatic polyesters containing cardo decahydronaphthalene groups. Eur Polym J 46:709–718

    Article  CAS  Google Scholar 

  29. More AS, Naik PV, Kumbhar KP, Wadgaonkar PP (2010) Synthesis and characterization of polyesters based on 1,1,1-[bis(4-hydroxyphenyl)-4′-pentadecylphenyl]ethane. Polym Int 59:1408–1414

    Article  CAS  Google Scholar 

  30. Honkhambe PN, Biyani MV, Bhairamadgi NS, Wadgaonkar PP, Salunkhe MM (2010) Synthesis and characterization of new aromatic polyesters containing pendent naphthyl units. J Appl Polym Sci 117:2545–2552

    CAS  Google Scholar 

  31. Latha G, Natarajan M, Balaji K, Murugavel SC (2014) Synthesis, spectral and thermal characterization of polyester derived from 1,1-bis(4-hydroxyphenyl)cyclohexane. High Perform Polym 26:125–134

    Article  Google Scholar 

  32. Tawade BV, Salunke JK, Sane PS, Wadgaonkar PP (2014) Processable aromatic polyesters based on bisphenol derived from cashew nut shell liquid: synthesis and characterization. J Polym Res 21:617

    Article  Google Scholar 

  33. Latha G, Murugavel SC (2016) Synthesis and characterization of cardo poly (ether-ester)s containing 1,1-bis (4-hydroxyphenyl) cyclohexane in the main chain. Polym Bull 73:3237–3253

    Article  CAS  Google Scholar 

  34. Gao C, Wei MH, Liu XL, Huang ZZ, Sheng SR (2016) Preparation and characterization of new aromatic poly(ether ester)s bearing cardo xanthene groups. High Perform Polym 29:1185–1191

    Article  Google Scholar 

  35. Bapat SP, Jadhav SA, Valsange NG, Tawade BV, Honkhambe PN, Chavan NN, Wadgaonkar PP (2017) Aromatic polyesters containing pendent 4-(phenylsulfonyl)phenyl groups: synthesis and characterization. J Polym Res 24:57

    Article  Google Scholar 

  36. Wu Z, Zhang G, Yan GM, Lu JH, Yang J (2018) Aromatic polyesters containing different content of Thioether and methyl units: facile synthesis and properties. J Polym Res 25:170

    Article  Google Scholar 

  37. Liu B, Yu WL, Lai YH, Huang W (2000) Synthesis of a novel cationic water-soluble efficient blue photoluminescent conjugated polymer. Chem Commun 7:551–552

    Article  Google Scholar 

  38. Yildirim M, Kaya I (2011) Synthesis and characterization of a novel kind soluble, conjugated, and fluorescent chelate polymer containing fluorene ring in the backbone: optical, electrical, and electrochemical properties. Synth Met 161:13–22

    Article  CAS  Google Scholar 

  39. Sakurai K, Fuji M (2000) Optical properties of a low birefringence polyester containing fluorene side chain I. Polym J 32(8):676–682

    Article  CAS  Google Scholar 

  40. Seesukphronrarak S, Kawasaki S, kobori K, Takata T (2008) Fluorene-rich high performance polyesters: synthesis and characterization of 9,9-fluorenylidene and 2,7-Fluorenylene-based polyesters with excellent optical property. J Polym Sci A Polym Chem 46:2549–2556

    Article  CAS  Google Scholar 

  41. Meng SY, Sun NW, Su KX, Feng F, Wang SL, Wang DM, Zhao XG, Zhao HW, Chen CH (2017) Optically transparent polyamides bearing phenoxyl, diphenylamine and fluorene units with high-contrast of electrochromic and electrofluorescent behaviors. Polymer 116:89–98

    Article  CAS  Google Scholar 

  42. Armargeo WLF, Perrin DD (1996) Purification of laboratory chemicals4th edn. Butterworth-Heinemann, Oxford

    Google Scholar 

  43. Pessan LA, Koros WJ (1993) Isomer effects on transport properties of polyesters based on bisphenol-a. J Polym Sci B Polym Phys 31:1245–1252

    Article  CAS  Google Scholar 

  44. Sundararajan PR (1990) Correlation between conformational features and the glass transition temperatures for a homologous series of polycarbonates. Macromolecules 23:2600–2602

    Article  CAS  Google Scholar 

  45. Aitken CL, Mchattie JS, Paul DR (1992) Dynamic mechanical behavior of polysulfones. Macromolecules 25:2910–2922

    Article  CAS  Google Scholar 

  46. Chan LW, Hao JS, Heng PWS (1999) Evaluation of permeability and mechanical properties of composite polyvinyl alcohol films. Chem Pharm Bull 47(10):1412–1416

    Article  CAS  Google Scholar 

  47. Jantrawut P, Chaiwarit T, Jantanasakulwong K, Brachais CH, Chambin O (2017) Effect of plasticizer type on tensile property and in vitro indomethacin release of thin films based on low-methoxyl pectin. Polymers 9:289

    Article  Google Scholar 

  48. Jeong SH, Lee JW, Lee SB, Boo JH (2003) Deposition of aluminum-doped zinc oxide films by RF magnetron sputtering and study of their structural, electrical and optical properties. Thin Solid Films 435:78–82

    Article  CAS  Google Scholar 

  49. Zou F, Wen H, Yan T, Cai M (2016) Synthesis and properties of novel soluble aromatic polyamides containing 4-aryl-2,6-diphenylpyridine moieties and pendant fluorinated phenoxy groups. J Polym Res 23:225

    Article  Google Scholar 

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Acknowledgements

The authors are acknowledged to Prof.R.C.Tandel, Head of Applied Chemistry Department for his kind help throughout the work. Authors are also thankful to Dr.Aadhar Mandot, Asst.Professor in Textile Engineering for his help in experimental work.

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  1. Applied Chemistry Department, Faculty of Technology and Engineering, The Maharaja Sayajirao University of Baroda, Vadodara, Gujarat, India

    Yogeshwar K. Chamkure & Rakesh K. Sharma

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  1. Yogeshwar K. Chamkure
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  2. Rakesh K. Sharma
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Correspondence to Rakesh K. Sharma.

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Chamkure, Y.K., Sharma, R.K. New organosoluble polyarylates containing pendent fluorene units: synthesis, characterization and thermal behaviour. J Polym Res 26, 17 (2019). https://doi.org/10.1007/s10965-018-1679-z

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