Aromatic polyesters with photosensitive side chains: Synthesis, characterization and properties

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Marioara Nechifor

Abstract

New aromatic polyesters with photosensitive groups in their pendant chains were prepared from a diphenol carrying as substituent a cinnamoyl group extended with a flexible oxyethyleneoxy spacer and different aromatic dicarboxylic acids via direct polyesterification reaction in the presence of the tosyl chloride/pyridine/dimethylformamide system as condensing agent. The resulting polyesters were characterized using Fourier-transform IR, proton and carbon nuclear magnetic resonance and ultraviolet spectroscopy, differential scanning calorimetry, thermogravimetric analysis, wide-angle X-ray diffracto­metry, gel permeation chromatography, viscosity measurement and solubility tests. These polyarylates had moderate inherent viscosities ranging from 0.37 to 0.54 dL g-1, good solubility in polar aprotic solvents, and afforded trans­parent, colorless and apparently tough films on casting from their solutions. Their glass-transition temperatures ranged from 136 to 154 °C. None of them showed significant decomposition below 320 °C and all retained 38–47 % of their weight at 700 °C in a nitrogen atmosphere. The presence of cinnamoyl chromophore endowed these polymers with the ability to interact with ultra­violet light, which resulted in photodimerization between the cinnamoyl side groups upon irradiation at l = 365 nm and cross-linking of the polymers chains without the necessity of photo-initiators or photosensitizers. Consequently, the polymer films became insoluble in organic solvents.

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How to Cite
[1]
M. Nechifor, “Aromatic polyesters with photosensitive side chains: Synthesis, characterization and properties”, J. Serb. Chem. Soc., vol. 81, no. 6, pp. 673–685, Jul. 2016.
Section
Polymers

References

D.-J. Liaw, P.-S. Chen, J. Polym. Sci.: Part A: Polym. Chem. 34 (1996) 885

S.-H. Hsiao, J.-H. Chiou, Polym. J. 33 (2001) 95

A. Rahmatpour, J. Polym. Res. 18 (2011) 1813

S. Seesukphronrarak, S. Kawasaki, K. Kobori, T. Takata, J. Polym. Sci.: Part A: Polym. Chem. 46 (2008) 2549

S. Watanabe, H. Murayama, M. Murata, Y. Masuda, M. Tanabe, Y. Imai, J. Polym. Sci.: Part A: Polym. Chem. 36 (1998) 2229

R. Seto, T. Kojima, K. Hosokawa, Y. Koyama, G. Konishi, Polymer 51 (2010) 4744

D.-J. Liaw, B.-Y. Liaw, J.-J. Hsu, Y.-C. Cheng, J. Polym. Sci.: Part A: Polym. Chem. 38 (2000) 4451

M. I. Loria-Bastarrachea, H. Vazquez-Torre, M. de J. Aguilar-Vega, J. Appl. Polym. Sci. 86 (2002) 2515

V. B. Patil, M. Medhia, N. S. Bhairamadgib, P. P. Wadgaonkarb, N.N. Maldara, Mater. Sci. Eng., B 168 (2010) 186

P. N. Honkhambe, M. V. Biyani, N. S. Bhairamadgi, P. P. Wadgaonkar, M. M. Salunkhe, J. Appl. Polym. Sci. 117 (2010) 2545

Z.-Z. Huang, X.-L. Pei, T. Wu, S.-R. Sheng, S.-Y. Lin, C.-S. Song, J. Appl. Polym. Sci. 119 (2011) 702

S. Mallakpour, S. Sepehri, J. Appl. Polym. Sci. 110 (2008) 2942

J. Chen, R A. Vaino, R. L. Smith, S. C. Collins, J. Polym. Sci.: Part A: Polym. Chem. 46 (2008) 3482

I. Assaid, D. Bosc, I. Hardy, J. Phys. Chem., B 108 (2004) 2801

S. Furumi, A. Otomo, S. Yokoyama, S. Mashiko, Thin Solid Films 438 –439 (2003): 85

S.-J. Sung, J. H. Yun, S. Lee, J.-K. Park, D.-H. Kim, K. Y. Cho, React. Funct. Polym. 70 (2010) 622

C.-M. Dong, X. Wu, J. Caves, S. S. Rele, B. S. Thoma, E. L. Chaikof, Biomater. 26 (2005) 4041

M. Nagata, E. Ioka, React. Funct. Polym. 63 (2005) 163

P. Gupta, S. R. Trenor, T. E. Long, G. L. Wilkes, Macromolecules 37 (2004) 9211

A. Reiser, Photoreactive polymers: The Science and Technology of Resists, Wiley, New York, 1989

N. Kawatsuki, K. Matsuyoshi, M. Hayashi, H. Takatsuka, T. Yamamoto, Chem. Mater. 12 (2000) 1549

M. Kato, K. Kanda, T. Kimura, H. Matsuda, H. Nakanishi, Polym. Bull. 36 (1996) 415

S. Mallakpour, E. Kowsari, J. Appl. Polym. Sci. 101 (2006) 455

F. Higashi, R. Hayashi, T. Yamazaki, J. Appl. Polym. Sci. 86 (2002) 2607

T. Kimura, J.-Y. Kim, T. Fukuda, H. Matsuda, Macromol. Chem. Phys. 203 (2002) 2344

B. Chae, S. W. Lee, M. Ree, Y. M. Jung, S. B. Kim, Langmuir 19 (2003) 687.