Abstract
Catalytic oxidative polymerization of 2,2′-dihydroxybiphenyl (DHBP) was performed by using Schiff base polymer-Cu (II) complex and hydrogen peroxide as catalyst and oxidant, respectively. According to size exclusion chromatography (SEC) analysis, the number-average molecular weight (M n), weight-average molecular weight (M w) and polydispersity index (PDI) values of poly (2,2′-dihydroxybiphenyl) (PDHBP) were found to be 37,500, 90,000 g mol−1 and 2.4, respectively. The thermal degradation kinetics was investigated by thermogravimetric analysis in dynamic nitrogen atmosphere at four different heating rates: 5, 10, 15 and 20 °C min−1. The derivative thermogravimetry curves of PDHBP showed that its thermal degradation process had one weight-loss step. The apparent activation energies of thermal decomposition for PDHBP as determined by Tang, Flynn–Wall–Ozawa (FWO), Kissenger–Akahira–Sunose (KAS), Coats–Redfern (CR) and Invariant kinetic parameter (IKP) methods were 109.1, 109.0, 110.0, 108.4 and 109.8 kJ mol−1, respectively. The mechanism function and pre-exponential factor were determined by master plots and Criado–Malek–Ortega method. The most likely decomposition process was a D n Deceleration type in terms of the CR, master plots and Criado–Malek–Ortega results.
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References
Xu MH, Lin ZM, Pu L (2001) Construction of an ortho-phenol polymer. Tetrahedron Lett 42(36):6235–6238
Higashimura H, Kubota M, Shiga A, Kodera M, Uyama H, Kobayashi S (2000) “Radical-controlled” oxidative polymerization of 4-phenoxyphenol catalyzed by a dicopper complex of a dinucleating ligand. J Mol Catal A Chem 161:233–237
Kurisawa M, Chung JE, Uyama H, Kobayashi S (2003) Thermo- and pH-responsive biodegradable poly(alpha-N-substituted gamma-glutamine)s. Biomacromolecules 4:1394–1399
Kobayashi S, Higashimura H (2003) Oxidative polymerization of phenols revisited. Prog Polym Sci 28:1015–1048
Ikeda R, Maruichi N, Tonami H, Tanaka H, Uyama H, Kobayashi S (2000) Peroxidase-catalyzed polymerization of fluorine-containing phenols. J Macromol Sci Pure Appl Chem 37(9):983–995
Tonami H, Uyama H, Kobayashi S, Fujita T, Taguchi Y, Osada K (2000) Chemoselective oxidative polymerization of m-ethynylphenol by peroxidase catalyst to a new reactive polyphenol. Biomacromolecules 1(2):149–151
Kobayashi S, Uyama H, Kimura S (2001) Enzymatic polymerization. Chem Rev 101(12):3793–3818
Tonami H, Uyama H, Oguchi T, Higashimura H, Kobayashi S (1999) Synthesis of a soluble polyphenol by oxidative polymerization of bisphenol-A using iron-salen complex as catalyst. Polym Bull 42(2):125–129
Saito K, Sun G, Nishide H (2007) Green synthesis of soluble polyphenol: oxidative polymerization of phenol in water. Green Chem Lett Rev 1(1):47–51
Uyama H, Maruichi N, Tonami H, Kobayashi S (2002) Peroxidase-catalyzed oxidative polymerization of bisphenols. Biomacromolecules 3(1):187–193
Oguchi T, Tawaki S, Uyama H, Kobayashi S (1999) Soluble polyphenol. Macromol Rapid Commun 20(7):401–403
Bilici A, Kaya İ, Doğan F (2009) Monomer/polymer Schiff base copper (II) complexes for catalytic oxidative polymerization of 2,2′-dihydroxybiphenyl. J Polym Sci Part A Polym Chem (accepted)
Demir HÖ, Kaya İ, Saçak M (2008) The oxidative polycondensation of 2-[(4-pyridilmethylene)-imino]phenol by molecular O-2 in alkaline medium: synthesis and characterization. Polym Bull 60(1):37–48
Demir HÖ (2006) Polymerization of pyridilazomethinphenols. PhD Thesis, Ankara University, Ankara, Turkey
Flynn J, Wall L (1966) A quick, direct method for the determination of activation energy from thermogravimetric data. Polym Lett 4(5):323–328
Ozawa T (1965) A new method of analyzing thermogravimetric data. Bull Chem Soc Jpn 38:1881–1888
Doyle CJ (1961) Synthesis and evaluation of thermally stable polymers. II. Polymer evaluation. Appl Polym Sci 5:285–292
Coats A, Redfern J (1964) Kinetics parameters from thermogravimetric data. Nature 201:68–69
Criado J, Malek J, Ortega A (1989) Applicability of the master plots in kinetic analysis of non-isothermal data. Thermochim Acta 147(2):377–385
Nunez L, Fraga F, Villanueva M (2000) Thermogravimetric study of the decomposition process of the system BADGE (n=0)/1,2 DCH. Polymer 41:4635–4641
Tang W, Liu Y, Zhang CH, Wang C (2003) New approximate formula for Arrhenius temperature integral. Thermochim Acta 408(1–2):39–43
Kissinger HE (1957) Reaction kinetics in different thermal analysis. Anal Chem 29(11):1702–1709
Levchik SV, Levchik GF, Lesnikovich AL (1985) Analysis and development of effective invariant kinetic-parameters finding method based on the non-isothermal data. Thermochim Acta 92:157–160
Gotor FJ, Criado JM, Malek J, Koga N (2000) Kinetic analysis of solid-state reactions: the universality of master plots for analyzing isothermal and nonisothermal experiments. J Phys Chem A 104(46):10777–10782
Perez-Maqueda LA, Criado JM, Gotor FJ, Malek J (2002) Advantages of combined kinetic analysis of experimental data obtained under any heating profile. J Phys Chem A 106(12):2862–2868
Wanjun T, Yuwen L, Hen Z, Zhiyong W, Cunxin W (2003) New temperature integral approximate formula for non-isothermal kinetic analysis. J Therm Anal Cal 74(1):309–315
Wanjun T, Yuwen L, Xi Y, Cunxin W (2004) Kinetic studies of the calcination of ammonium metavanadate by thermal methods. Ind Eng Chem Res 43(9):2054–2059
Criado JM, Malek J, Ortega A (1989) Applicability of the master plots in kinetic-analysis of non-isothermal data. Thermochim Acta 147(2):377–385
Senum GI, Yang KT (1977) Rational approximations of the integral of the Arrhenius function. J Therm Anal 11(13):445–447
Lesnikovich AL, Levchik SV (1985) Invariant kinetic-parameters of polybutadiene binders thermal-decomposition. J Propul Power 1(4):311–312
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Doğan, F., Kaya, İ. & Bilici, A. Non-isothermal degradation kinetics of poly (2,2′-dihydroxybiphenyl). Polym. Bull. 63, 267–282 (2009). https://doi.org/10.1007/s00289-009-0084-5
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DOI: https://doi.org/10.1007/s00289-009-0084-5