Synthesis and Characterization of Cholesteric Thermotropic Liquid Crystalline Polyesters Based on Isosorbide
Nayaku N. Chavan
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DOI: 10.4236/msa.2011.210205   PDF    HTML     5,520 Downloads   9,901 Views   Citations

Abstract

BACKGROUND: Generally main chain cholesteric thermotropic liquid crystalline polymers are prepared form chiral diacid or diol monomer. But these monomers are costly. Isosorbide is chiral cycloaliphatic diol accessible from renewable resources in the form of pure enantiomers. Thus it is used to synthesize main chain cholesteric thermotropic liquid crystalline polymers. Incorporation of phenyl hydroquinone into the backbone of the main chain frustrates chain packing, thus lowering the crystallinity and depressing the melting point below the degradation temperature, also improves the solubility due to disruption of packing and maintains the mechanical and thermal performance. RESULTS: Optical microscopy study reveals that more than 50% of isosorbide content with phenyl hydroquinone and terephthalic acid showed “yellow iridescent oily streaks” with a background of mosaic/marble texture. These are the typical textures of cholesteric liquid crystalline phase. Copolyesters based on phenyl hydroquinone, isosorbide and terephthalic acid are soluble in aprotic solvents like N,N-dimethylacetamide (DMAC), dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), and N-methyl-2-pyrrolidone (NMP). Solubility increases with the content of isosorbide percent. Thermal stability of all copolyesters was more than 300?C on the basis of 10% wt loss. CONCLUSIONS: It was found that main chain cholesteric thermotropic liquid crystalline polymers can be prepared form chiral cycloaliphatic diol such as isosorbide. Main chain cholesteric thermotropic liquid crystalline polyesters are prepared from phenyl hydroquinone, isosorbide and terephthalic acid showed thermal stability more than 300?C. Main chain cholesteric thermotropic liquid crystalline polymers are soluble in aprotic solvents like DMAC, DMSO, DMF and NMP.

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N. Chavan, "Synthesis and Characterization of Cholesteric Thermotropic Liquid Crystalline Polyesters Based on Isosorbide," Materials Sciences and Applications, Vol. 2 No. 10, 2011, pp. 1520-1527. doi: 10.4236/msa.2011.210205.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] V. Shibaev, A. Bobrovsky and N. Boiko, “Photoactive Liquid Crystalline Polymer Systems with Light-Control- lable Structure and Optical Properties,” Progress in Poly- mer Science, Vol. 28, No. 5, 2003, pp. 729-836. doi:10.1016/S0079-6700(02)00086-2
[2] S. Nakanishi and M. Ueda, “Synthesis of Novel Glass-Form- ing Liquid Crystals Containing Acrylic Acid Trimer Core Unit and Mesogenic Moiety, and Their Use in Cholesteric Reflection Films,” Polymer Journal, Vol. 39, No. 3, 2007, pp. 252-258. doi:10.1295/polymj.PJ2006115
[3] B. Zhang, J. Hu, B. Wang, D. Yao and H. Li, “Synthesis and Characterization of Side-Chain Cholesteric Elastomers Derived from an Isosorbide Cross Linking Agent,” Colloid & Polymer Science, Vol. 285, No. 15, 2007, pp. 1683-1690. doi:10.1007/s00396-007-1742-5
[4] J. Lub, W. P. M. Nijssen, R. T. Wegh, J. P. A. Vogels and A. Ferrer, “Synthesis and Properties of Photoisomerizable Derivatives of Isosorbide and Their Use in Cholesteric Filters,” Advanced Functional Materials, Vol. 15, No. 12, 2005, pp. 1961-1972. doi:10.1002/adfm.200500127
[5] S. A. Jadhav, R. R. Chougule, Y. A. Shinde and N. N. Chavan, “Synthesis and Characterization of Cholesteric Thermotropic Liquid Crystalline Polyesters,” Journal of Applied Polymer Science, Vol. 103, No. 2, 2007, pp. 1232-1237. doi:10.1002/app.24610
[6] H. Finklemenn, H. Ringsdorf, W. Siol and J. H. Wendorff, “Synthesis of Cholesteric Liquid Crystalline Polymers,” Macromolecular Chemistry, Vol. 179, No. 3, 1978, pp. 829-832. doi:10.1002/macp.1978.021790326
[7] J. Asrar, J. Toriumi, J. Watanabe, W. R. Krigbaum, A. Ciferri and J. Preston, “Thermotropic Homopolyesters. I. The Preparation and Properties of Polymers Based on 4,4’-Dihydroxybiphenyl,” Journal of Polymer Science Polymer Part B: Physics Edition, Vol. 21, No. 7, 1983, pp. 1119-1131. doi:10.1002/pol.1983.180210712
[8] K. Fujishiro and R. W. Lenz, “Main-Chain Cholesteric Liquid Crystalline Polyesters with Chiral Pendant Groups. 1. Model Compounds and Polyesters Containing a Chiral Substituted Hydroquinone,” Macromolecules, Vol. 25, No. 1, 1992, pp. 81-87. doi:10.1021/ma00027a014
[9] H. Park, J. Jin and R. W. Lenz, “Liquid Crystal Polymers: 19. Cholesteric Main Chain Polyesters with Triad Aromatic Ester Mesogenic Units and Chiral Polyalkaline Spacers,” Polymer, Vol. 26, No. 9, 1985, pp. 1301-1306. doi:10.1016/0032-3861(85)90303-9
[10] N. Khan, Z. Bashir and D. M. Price, “Liquid Crystalline Aromatic Polyesters Formed with Terephthalic Acid, Phenyl Hydroquinone, and Naphthalene or Anathracene Diols,” Journal of Applied Polymer Science, Vol. 58, No. 9, 1995, pp. 1509-1516. doi:10.1002/app.1995.070580913
[11] H. R. Kricheldorf and N. Probst, “Liquid-Crystalline Polyimides. 16. Chiral Thermotropic Copoly(Ester-Imide)s Based on Isosorbide and N-(4-Carboxyphenyl) trimel- litimide,” Macromolecular Rapid Communications, Vol. 16, No. 4, 1995, pp. 231-237. doi:10.1002/marc.1995.030160401
[12] G. Schwarz and H. R. Kricheldorf, “New Polymer Synthesis. LXXXIII. Synthesis of Chiral and Cholesteric Polyesters from Silylated ‘Sugar Diols’,” Journal of Polymer Science Part A: Polymer Chemistry Edition, Vol. 34, No. 4, 1996, pp. 603-611. doi:10.1002/(SICI)1099-0518(199603)34:4<603::AID-POLA6>3.0.CO;2-R
[13] H. R. Kricheldorf, S. Sun, A. Gerken and T. Chang, “Polymers of Carbonic Acid. 22. Cholesteric Polycarbonates Derived from (S)-((2-Methylbutyl)thio)hydroqui- none or Isosorbide,” Macromolecules, Vol. 29, No. 25, 1996, pp. 8077-8082. doi:10.1021/ma960494d
[14] Q. Lin, J. Pasatta and T. E. Long, “Synthesis and Characterization of Chiral Liquid-Crystalline Polyesters Containing Sugar-Based Diols via Melt Polymerization,” Journal of Polymer Science Part A: Polymer Chemistry Edition, Vol. 41, No. 16, 2003, pp. 2512-2520. doi:10.1002/pola.10787
[15] B. Zhang, Y. Zheng and H. Lu, “Synthesis and Characterization of Side Chain Cholesteric Liquid Crystalline Polymers Containing Isosrbide as a Chiral Center,” Liquid Crystals, Vol. 32, No. 3, 2005, pp. 357-364. doi:10.1080/02678290500034065
[16] M. Flugel and W. Heitz, “Synthesis and Properties of Polyamides Based on (±)-Nonbornane-2 Endo, 3 Exo-di- carboxylic Acid,” Macromolecular Rapid Communications, Vol. 18, No. 6, 1997, pp. 523-528. doi:10.1002/marc.1997.030180611

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