High-Performance Polyesters: Synthesis, Characterization, and Properties of Poly(P-Oxybenzoate)

Abstract:

Poly (p-oxybenzoate) samples were synthesized via the esterification and the transesterification reactions. The structure of the obtained target products was investigated by IR spectroscopy and has revealed that these substances were oligomers. The transesterification method has facilitated the synthesis of higher molecular weight grades of the polymer. This resulted in enhanced thermal properties of polyester synthesized by transesterification (up to 340 °C). The other specimen has performed thermal stability up to 320 °C.

• Periodical: Materials Science Forum (Volume 992)
• Pages: 380-385
• DOI: https://doi.org/10.4028/www.scientific.net/MSF.992.380
• Online since: May 2020
• Authors: Alsu I. Akhmetshina*, Liana K. Karimova, R.Ya. Deberdeev
• Keywords: High-Performance Polymers, Liquid Crystalline Polymers, Polycondensation, Thermal Stability

References

[1] J. Wang, Y.-H. Ding, W.-Z. Zhao, S.-H. Yu, Z.-P. Ji, Preparation and performance of lubrication composite coating based on poly(4-oxybenzoyl) (I), Surface Engineering. 27 (2011) 164-168.

DOI: 10.1179/026708410x12459349720015

[2] H. Cheng, X. Cheng, Mechanical and tribological properties of MWCNTs-reinforced thermoplastic poly(p-oxybenzoate) composites, Journal of Reinforced Plastics and Composites. 31 (2012) 785-795.

DOI: 10.1177/0731684412444910

[3] P. Damman, M. Dosière, J. C. Wittmann, Epitaxial Polymerization of Poly(p-oxybenzoate) on Friction-Transfer Poly(tetrafluoroethylene) Substrates, Macromolecules. 30 (1997) 8386–8391.

DOI: 10.1021/ma9710343

[4] A.K. Sarker, K. Kimura, Y. Yamashita, Preparation of Poly(p-oxybenzoyl) Whisker in Paraffin Wax, Polymer Journal. 34 (2002) 426-436.

DOI: 10.1295/polymj.34.426

[5] K. Kimura, S.Kohama, S.Kondoh, T. Uchida, Y. Yamashita, T. Oohazama, Y.Sakaguchi, Novel network morphology of poly(p-oxybenzoyl), Journal of Polymer Science Part A: Polymer Chemistry. 43 (2005) 1624-1634.

DOI: 10.1002/pola.20639

[6] F. Rybnikar, B.-L. Yuan, P.H. Geil, Lamellar crystallization during bulk polymerization of poly(p-oxybenzoate), Polymer. 35 (1994) 1863-1868.

DOI: 10.1016/0032-3861(94)90975-x

[7] J. Liu, B.-L. Yuan, P.H. Geil, D.L. Dorset, Chain conformation and molecular packing in poly(p-oxybenzoate) single crystals at ambient temperature, Polymer. 38 (1997) 6031-6047.

DOI: 10.1016/s0032-3861(97)00161-4

[8] W. Jian, Z. Wenzhen, G. Chaowei, Fabrication and properties of a lubrication composite coating based on poly(p-hydroxybenzoic acid) (PHBA), Journal of Materials Science. 44 (2009) 227-233.

DOI: 10.1007/s10853-008-3082-3

[9] J. Wang, Y.Y. Guo, W.Z. Zhao, Chemical characterisation of polyoxybenzoate matrix composite materials by high performance liquid chromatography, Plastics, Rubber and Composites. 40 (2011) 116-120.

DOI: 10.1179/174328911x12948334590240

[10] S. Wang, Q. Li, S. Zhang, L. Pan, Tribological behavior of poly (phenyl p-hydroxybenzoate)/polytetrafluoroethylene composites filled with hexagonal boron nitride under dry sliding condition, Materials & Design. 43 (2013) 507-512.

DOI: 10.1016/j.matdes.2012.07.048

[11] Q. Ding, Y. Zhang, G. Zhao, F. Wang, Properties of POB reinforced PTFE-based friction material for ultrasonic motors, Journal of Polymer Engineering. 37 (2017).

DOI: 10.1515/polyeng-2016-0183

[12] F.Y. Sun, Q.M. Wang, J.J. Qu, Mechanical and Tribological Properties of Fiber Reinforced Ekonol Composites, Advanced Materials Research. 219-220 (2011) 337-340.

DOI: 10.4028/www.scientific.net/amr.219-220.337

[13] M. Hribova, F. Rybnikar, P.H. Geil, The Effect of Solid Sheet Fillers on Poly-p-Oxybenzoate Polymerization, Crystallization and Structure, Journal of Macromolecular Science, Part B. 48 (2009) 562-572.

DOI: 10.1080/00222340902837709

[14] A.K. Sarker, K. Kimura, F. Yokoyama, Y. Yamashita, Control of the Length of Aromatic Polyester Whiskers, High Performance Polymers. 13 (2001) 354-364.

DOI: 10.1088/0954-0083/13/2/330

[15] A.K. Sarker, K. Kimura, S. Uchida, Y. Yamashita, Size Control of Poly(p -Oxybenzoyl) Whiskers by Addition of Crystals during Polymerization of p -Acetoxybenzoic Acid, High Performance Polymers. 14 (2002) 155-167.

DOI: 10.1177/095400830201400105

[16] K. Kimura, T. Horii, Y. Yamashita, Morphology of Poly(p-oxybenzoyl) Crystal Prepared by Direct Polycondensation of p-Hydroxybenzoic Acid with p-Toluenesulfonyl Chloride in Pyridine, Journal of Polymer Science Part A: Polymer Chemistry. 41 (2003) 3275-3282.

DOI: 10.1002/pola.10916

[17] K. Kimura, T. Horii, Y. Yamashita, Morphology of Poly(p-oxybenzoyl) Crystals Prepared by Direct Polycondensation of p-Hydroxybenzoic Acid with Diphenyl Chlorophosphate. 15 (2003) 167-179.

DOI: 10.1177/0954008303015002002

[18] H.R. Kricheldorf, G. Schwarz, New polymer syntheses, 7†, Synthesis and characterization of oligomeric and high molecular weight poly(4‐hydroxybenzoate), Makromolekulare Chemie. 184 (1983) 475-496.

[19] M. Kihara, S.-I. Kohama, S. Umezono, K. Wakabayashi, S. Yamazaki, K. Kimura, Preparation of poly(p-oxybenzoyl) crystals using direct polymerization of p-hydroxybenzoic acid in the presence of boronic anhydrides, Journal of Polymer Science Part A: Polymer Chemistry. 49 (2011) 1088-1096.

DOI: 10.1002/pola.24521

[20] M. Kihara, Y. Sakakiyama, S. Yamazaki, K. Kimura, Preparation of aromatic polyesters by direct polymerization in the presence of boronic anhydride under non-stoichiometric condition, Polymer 66. (2015) 222-229.

DOI: 10.1016/j.polymer.2015.04.019

[21] J.Y. Kim, Carbon Nanotube-Reinforced Thermotropic Liquid Crystal Polymer Nanocomposites, Materials. 2 (2009) 1955-1974.

DOI: 10.3390/ma2041955

[22] M. Kutz, Handbook of Environmental Degradation of Materials, Elsevier, Cambridge, (2018).