Thermotropic Liquid Crystalline Behavior of Hydroxypropyl Celluloses Bearing Cholesteryl and Nitroazobenzene Groups

콜레스테릴과 니트로아조벤젠 그룹을 지닌 히드록시프로필 셀룰로오스들의 열방성 액정 거동

  • Jeong, Seung-Yong (Department of Polymer Science and Engineering, Dankook University) ;
  • Ma, Yung-Dae (Department of Polymer Science and Engineering, Dankook University)
  • 정승용 (단국대학교 고분자공학과) ;
  • 마영대 (단국대학교 고분자공학과)
  • Published : 2008.09.30

Abstract

Three kinds of hydroxypropyl cellulose (HPC) derivatives: 6- (cholesteryloxycarbonyl) pentoxypropyl celluloses(CHPCs) with degree of esterification(DE) ranging from 0.6 to 3, 6-[4-{4'-(nitrophenylazo)phenoxycarbonyl}] pentoxypropyl celluloses (NHPCs) with DE ranging from 0.4 to 3, and fully 6-(cholesteryloxycarbonyl) pentanoated NHPCs (CNHPCs) were synthesized, and their thermotropic liquid crystalline properties were investigated. All the CHPCs and NHPCs with $DE{\leq}1.7$ formed enantiotropic cholesteric phases, whereas CNHPCs with 6-(cholesteryloxycarbonyl) pentanoyl DE(DEC) more than 1.6 exhibited monotropic cholesteric phases. On the other hand, NHPCs with $DE{\geq}2.4$ and CNHPCs with $DEC{\leq}1.3$ showed monotropic nematic phases. NHPCs with $DE{\leq}l$, as well as HPC, formed right-handed helices whose optical pitches (${{\lambda}_m}'s$) increase with temperature, while all the CHPCs formed left-handed helices whose ${{\lambda}_m}'s$ decrease with temperature. In contrast with these derivatives, NHPCs with $1.4{\leq}DE{\leq}1.7$ and CNHPCs with $DEC{\geq}1.6$ did not display reflection colors over the full cholesteric range, suggesting that the helical twisting power of the cellulose chain and the cholesteryl group highly depends on the chemical structure and DE of mesogenic group.

세 종류의 히드록시프로필 셀룰로오스(HPC) 유도체들, 즉 에스터화도(DE)가 0.6에서 3의 범위에 있는 6-(콜레스테릴옥시카보닐)펜톡시프로필 셀룰로오스들(CHPEs), DE가 0.4에서 3의 범위에 있는 [6-4-{4'-(니트로페닐아조)펜옥시카보닐}] 펜톡시프로필 셀룰로오스들(NHPCs) 그리고 완전치환 6-(콜레스테릴옥시카보닐)펜타노화 NHPCs(CNHPCs)들을 합성함과 동시에 이들의 열방성 액정 특성들을 검토하였다. 모든 CHPCs 그리고 $DE{\leq}1.7$인 NHPCs는 쌍방성 콜레스테릭 상들을 형성하는 반면 6-(콜레스테릴옥시카보닐) 펜타노일 DE (DEC)가 1.6이상인 CNHPCs는 단방성 콜레스테릭 상들을 형성하였다. 한편, $DE{\geq}2.4$인 NHPCs 그리고 $DEC{\leq}3$인 CNHPCs는 단방성 네마틱 상들을 형성하였다. HPC와 동일하게, $DEC{\leq}1$인 NHPCs는 온도상승에 의해 광학피치들(${{\lambda}_m}'s$)이 증가하는 우측 방향의 나선구조를 형성하는 반면 모든 CHPCs는 온도상승에 의해 ${\lambda}_m$들이 감소하는 좌측방향의 나선구조를 형성하였다. 이들 유도체와 달리, $1.4{\leq}DE{\leq}1.7$인 NHPCs 그리고 $DEC{\geq}1.6$인 CNHPEs는 콜레스테릭 상의 전 범위에서 반사 색깔을 나타내지 않았다. 이러한 사실은 셀룰로오스 사슬 그리고 콜레스테릴 그룹에 의한 나선의 비틀림력은 mesogenic 그룹의 화학구조와 DE에 민감하게 의존함을 시사한다.

Keywords

References

  1. K. Shimamura, J. L. White, and J. F. Fellers, J. Appl. Polym. Sci., 26, 2615 (1981)
  2. S.-L. Tseng, A. Valente, and D. G. Gray, Macromolecules, 14, 715 (1982) https://doi.org/10.1021/ma50004a049
  3. C, Jianan, H. Yifang, Y. Jinyue, Y. Shaoqiong, and Y. Hua, J. Appl. Polym. Sci., 45, 2153 (1992) https://doi.org/10.1002/app.1992.070451211
  4. Y. Huang, J. Appl. Polym. Sci., 51, 1979 (1994) https://doi.org/10.1002/app.1994.070511114
  5. T. Fukada, A. Takada, and T. Miyamoto, Cellulosic Polymers, Blends and Composites, R. D. Gilbert, Editor, Hanser Verlag, Munich, Chap 3, p 47 (1994)
  6. T. Fukada, Y. Tsujii, and T. Miyamoto, Macromol. Symp., 99, 257 (1995)
  7. P. Zugenmaier, Handbook of Liquid Crystals, D. Demus, J. Goodby, G. W. Gray, H.-W. Spiess, and V. Vill, Editors, Wiley-VCH, Weinheim-New York, Vol 3, Chap IX, p 453 (1998)
  8. Q. Zhoi, L. Zhang, H. Okamura, M. Minoda, and T. Miyamoto, J. Polym. Sci. Part A: Polym. Chem., 39, 376 (2001) https://doi.org/10.1002/1099-0518(20010201)39:3<376::AID-POLA1004>3.0.CO;2-Z
  9. S.-Y. Jeong, J.-H. Jeong, Y.-D. Ma, and Y. Tsujii, Polymer(Korea), 25, 279 (2001)
  10. Z. Yue and J. M. G. Cowie, Macromolecules, 35, 6572 (2002) https://doi.org/10.1021/ma0202787
  11. T.-A. Yamagishi, F. Guittard, M. H. Godinho, A. F. Martins, A. Cambon, and P. Sixou, Polym. Bull., 32, 47 (1994) https://doi.org/10.1007/BF00297413
  12. F. Guittard, T. Yamagishi, A. Cambon, and P. Sixou, Macromolecules, 27, 6988 (1994) https://doi.org/10.1021/ma00101a042
  13. V. Percec and C. Pugh, Side Chain Liquid Crystal Polymers, C. B. Mc Ardle, Editor, Chapmann and Hall, New York, Chap 3, p 30 (1989)
  14. R. Zentel, Handbook of Liquid Crystals, D. Demus, J. Goodby, G. W. Gray, H.-W. Spiess, and V. Vill, Editors, Wiley-VCH, Weinheim-New York, Vol 3, Chap 3, p 52 (1998)
  15. J.-H. Kim, S.-Y. Jeong, and Y.-D. Ma, Polymer(Korea), 28, 92 (2004)
  16. S.-Y. Jeong and Y.-D. Ma, Polymer(Korea), 32, 169 (2008)
  17. S.-Y. Jeong and Y.-D. Ma, Polymer(Korea), 31, 37 (2007)
  18. P. Zheng, X. Hu, X. Zhao, L. Li, K. C. Tam, and L. H. Gan, Macromol. Rapid Commun., 25, 678 (2004) https://doi.org/10.1002/marc.200300123
  19. X. Hu, P. Z. Zheng, X. Y. Zhao, L. Li, K. C. Tam, and L. H Gan, Polymer, 45, 6219 (2004) https://doi.org/10.1016/j.polymer.2004.05.072
  20. K. Arai and Y. Kawabata, Macromol. Rapid Commun., 16, 875 (1995) https://doi.org/10.1002/marc.1995.030161201
  21. M. Müller and R. Zentel, Macromol. Chem. Phys., 201, 2005 (2000)
  22. E. Yashima, J. Noguchi, and Y. Okamoto, Macromolecules, 28, 8368 (1995) https://doi.org/10.1021/ma00128a054
  23. M. Buchel and B. Weichart, Phys. Rev. E, 55, 455 (1997) https://doi.org/10.1103/PhysRevE.55.455
  24. S. Yang, M. M. Jacob, L. Li, A. L. Cholli, J. Kumar, and S. K. Tripathy, Macromolecules, 34, 9193 (2001) https://doi.org/10.1021/ma010931a
  25. N. Tamaoki, Adv. Mater., 13, 1135 (2001) https://doi.org/10.1002/1521-4095(200108)13:15<1135::AID-ADMA1135>3.0.CO;2-S
  26. V. Shibaev, A. Bobrovsky, and N. Boiko, Prog. Polym. Sci., 28, 729 (2003) https://doi.org/10.1016/S0079-6700(02)00086-2
  27. K. Ichimura, Chem. Rev., 100, 1847 (2000) https://doi.org/10.1021/cr980079e
  28. A. Natansohn and P. Rochon, Chem. Rev., 102, 4139 (2002) https://doi.org/10.1021/cr970155y
  29. R. Rosenhauer, Th. Fischer, J. Stumpe, R. Gimenez, M. Pinol, J. L. Serrano, A. Vinuales, and D. Broer, Macromolecules, 38, 2213 (2005) https://doi.org/10.1021/ma048259f
  30. R. Gimenez, M, Millaruelo, M. Pinol, J. L. Serrano, A. Vinuales, R. Rosenhauer, T. Fischer, and J. Stumpe, Polymer, 46, 9230 (2005) https://doi.org/10.1016/j.polymer.2005.07.040
  31. G. Iftime, A. Natansohn, and P. Rochon, Macromolecules, 35, 365 (2002) https://doi.org/10.1021/ma010477a
  32. T. Ikeda, M. Nakano, Y. Yu, O. Tsutsumi, and A. K. Kanazawa, Adv. Mater., 15, 201 (2003) https://doi.org/10.1002/adma.200390045
  33. M. Kondo, J. Mamiya, M. Kinoshita, and T. Ikeda, Mol. Cryst. Liq. Cryst., 478, 245 (2007) https://doi.org/10.1080/15421400701680952
  34. T. Yoshino, J. Mamiya, M. Kinoshita, T. Ikeda, and Y. Yu, Mol. Cryst. Liq. Cryst., 478, 233 (2007) https://doi.org/10.1080/15421400701681083
  35. M. Nakano, Y. Yu, A. Shishido, O. Tsutsumi, A. Kanazawa, T. Shiono, and T. Ikeda, Mol. Cryst. Liq. Cryst., 398, 1 (2003) https://doi.org/10.1080/15421400390220827
  36. S. Leclair, L. Mathew, M. Giguere, S. Motallebi, and Y. Zhao, Macromolecules, 36, 9024 (2003) https://doi.org/10.1021/ma034886d
  37. M. Moniruzzaman, G. F. Fernando, and J, D. R. Talbot, J. Polym. Sci. Part A: Polym. Chem., 42, 2886 (2004) https://doi.org/10.1002/pola.20108
  38. Y. Zhao, Y. Chenard, and N. Paiement, Macromolecules, 33, 1049 (2000) https://doi.org/10.1021/ma9912103
  39. L. Corvazier and Y. Zhao, Macromolecules, 32, 3195 (1999) https://doi.org/10.1021/ma981881l
  40. L. Chen, S.-G. Li, Y.-P. Zhao, Y.-C. Wang, and Q.-W. Wang, J. Appl. Polym. Sci., 96, 2163 (2005) https://doi.org/10.1002/app.21675
  41. S. Khoukh, R. Oda, Th. Labrot, P. Perrin, and C. Tribot, Langmuir, 23, 94 (2007) https://doi.org/10.1021/la061714b
  42. S.-Y. Jeong and Y.-D. Ma, Polymer(Korea), 30, 35 (2006) https://doi.org/10.1016/0032-3861(89)90379-0
  43. Y.-D. Ma and S.-Y. Jeong, Industrial Technology Research Paper(Dankook University), 6, 1 (2005)
  44. J.-X. Guo and D. G. Gray, Macromolecules, 22, 2082 (1989) https://doi.org/10.1021/ma00195a011
  45. J. C, Thies and J. M. G. Cowie, Polymer, 42, 1297 (2001) https://doi.org/10.1016/S0032-3861(00)00558-9
  46. S.-Y. Jeong, J.-H. Choi, and Y.-D. Ma, Polymer(Korea), 26, 523 (2002)
  47. S.-Y. Jeong and Y.-D. Ma, Polymer(Korea), 31, 356 (2007)
  48. S,-Y. Jeong and Y.-D, Ma, Industrial Technology Research Paper(Dankook University), 8, 69 (2007)
  49. J. L. Lee, E. M. Pearce, and T. K. Kwei, Macromolecules, 30, 8233 (1997) https://doi.org/10.1021/ma970647c
  50. Y.-D. Ma, Polym. Sci. Tech., 8, 555 (1997)
  51. T. Kaneko, H. Nagasawa, J. P. Gong, and Y. Osada, Macromolecules, 37, 187 (2004) https://doi.org/10.1021/ma035272b
  52. M. Li, E. Zhou, J. Xu, and X. Chen, J. Appl. Polym. Sci., 60, 2185 (1996) https://doi.org/10.1002/(SICI)1097-4628(19960620)60:12<2185::AID-APP16>3.0.CO;2-6
  53. T. Schleeh, C. T. Imrie, D. M. Rice, F. E. Karasz, and G. S. Attard, Polymer, 31, 1859 (1993) https://doi.org/10.1016/0032-3861(90)90007-L
  54. C. T. Imarie and B. J. A. Paterson, Macromolecules, 27, 6673 (1994) https://doi.org/10.1021/ma00100a063
  55. C. T. Imrie, F. E. Karasz, and G. S. Attard, Macromolecules, 27, 1578 (1994) https://doi.org/10.1021/ma00084a045
  56. S. Weidner, D. Wolff, and J. Springer, Liq. Cryst., 20, 587 (1996) https://doi.org/10.1080/02678299608031147
  57. H. Hattori and T. Uryu, J. Polym. Sci. Part A: Polym. Chem., 38, 887 (2000) https://doi.org/10.1002/(SICI)1099-0518(20000301)38:5<887::AID-POLA13>3.0.CO;2-G
  58. S. H. Chen and M. L. Tsai, Macromolecules, 23, 5055 (1990) https://doi.org/10.1021/ma00226a002
  59. Ya. S. Freidzon and V. P. Shibaev, Liquid-Crystal Polymers, N. A. Plate, Editor, Plenum Press, New York, Chap 7, p 251 (1993)
  60. T. Kodai, M. Endo, and M. Kurachi, Macromol. Chem. Phys., 199, 2329 (1998) https://doi.org/10.1002/(SICI)1521-3935(19981001)199:10<2329::AID-MACP2329>3.0.CO;2-G
  61. M. Sato and M. Mizoi, Polym. J., 36, 607 (2004) https://doi.org/10.1295/polymj.36.607
  62. S.-Y. Jeong and Y.-D. Ma, Polymer(Korea), 30, 35 (2006) https://doi.org/10.1016/0032-3861(89)90379-0
  63. S.-Y. Jeong and Y.-D. Ma, Polymer(Korea), 31, 58 (2007)
  64. H. de Vires, Acta Crystallogr., 4, 219 (1951) https://doi.org/10.1107/S0365110X51000751
  65. S. Chandrasekhar, Liquid Crystals, Cambridge University Press, Cambridge, Chap 4, p 213 (1992)
  66. J. Watanabe, M. Goto, and T. Nagase, Macromolecules, 20, 298 (1987) https://doi.org/10.1021/ma00168a011
  67. T. Yamagishi, Ph. D. dissertation, Kyoto University, 1989
  68. V. P. Shibaev, Ya. S. Freidzon, and G. S. Kostromin, Liquid Crystalline and Mesomorphia Polymers, V. P. Shibaev, and L. Lam, Editors, Springer-Verlag, New York, Chap 3, p 77 (1994)
  69. J.-H. Kim, S.-Y. Jeong, and Y.-D. Ma, Polymer(Korea), 28, 41 (2004)
  70. M. L. Tsai and S. H. Chen, Macromolecules, 33, 1908 (1990)
  71. S.-Y. Jeong and Y.-D. Ma, J. Korean Ind. Eng. Chem., 18, 475 (2007)
  72. S.-Y. Jeong and Y.-D. Ma, Polymer(Korea), 32, 230 (2008)