Synthesis,Characterization and Thermal Degradation Study of Terpolymer-derived from p-Hydroxybenzoic Acid,Diaminonaphthelein with Formaldehyde

Abstract

Resin pHDNF has been synthesized by the condensation of p-hydroxybenzoic acid and diaminonaphthelein with formaldehyde in the presence of catalyst hydrochloric acid in 1 : 1 : 2 molar proportions of reactants. The purity of newly synthesized terpolymer has been tested and confirmed by the thin layer chromatography (TLC) technique. Detailed thermal degradation studies of the pHDNF resin have been carried out to ascertain its thermal stability. The thermal degradation curve was examined in order to determine their mode of decomposition, order of reaction, apparent activation energy, frequency factor, free energy change, entropy change and apparent energy change. The Freeman—Carroll and Sharp—Wentworth methods were applied for the calculation of kinetic parameters and the data from the Freeman—Carroll method was been used to determine various thermodynamic parameters. The terpolymer resin was characterized by elemental analysis, infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy and UV-visible spectral studies. The number-average molecular weight of the resin was determined by non-aqueous conductometric titration.

Keywords

Synthesis degradation thermal properties degree of polymerization activation energy

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References

Colin F.P. and Rena M.P. (1987). Thermally stable, highly fluorinated stationary phases for gas chromatography, Analytica Chimica Acta Vol. 200 : 151-169.

Chandra R. , Rajabi L. and Soni R.K. (1996) The effect of bismaleimide resin on curing kinetics of epoxy-amine thermosets , J. of Appl. Polym. Sc., Vol. 62(4): 661-671.

Masram D.T. , Kariya K.P. and Bhave N.S. ( 2008). Thermal Degradation Study of Terpolymer Resin derived from Salicylicacid-Ethylenediamine-Formaldehyde. 16th DAE, BRNS symposium on thermal analysis Indira Gandhi center for Atomic research (IGCAR) Kalpakkam Thermans, Feb 4-8, 329-331.

Masram D.T. ( 2009). Thermal Degradation Study of Terpolymer Resin derived from Salicylic acid, Diaminonaphthalein, Formaldehyde Terpolymer. E-J. of Chemistry. 6(3): 830-834.

Das A.P. , Lenka, S. and Nayak, P.L. ( 1985). Synthetic resins: I. Preparation and characterization of resins from substituted benzoic acid-formaldehyde . J. Appl. Polym. Sci., 30: 4619.

Aristove L.J. and Kostantinov , V.V. (1961). Polymers with chelate bonding, derived from 8-quinolinol. Izu. Tomsk. Politekhn. Inst. 111: 104-6.

Samal, R.K. , Senapati, B.K. and Behuray T.B. ( 1996). Synthesis and Characterization of Aniline-Doped Mixed Copolymer Resins-2. J. Appl. Polym. Sci., 62: 655.

DeGeiso, R.C. , Donaruma, L.G. and Tomic, E.A. (1962). Polymeric Ligands, Separation of Uranium from Solutions and Ore Leaches with Salicylic Acid-Formaldehyde Polymers. Ind. Eng. Chem. Process Des. Dev., ACS pub., 2(1): 43-44.

Michael, P. , Lingala, P. , Juneja , H. and Paliwal, L. (2004). Synthetic, structural, and thermal degradation of a tercopolymer derived from salicylic acid, guanidine, and formaldehyde. J. Appl. polym. Sci. 92: 2278.

10.

Masram, D.T. , Kariya, K.P. and Bhave, N.S. (2010). Kinetics of Thermal Degradation Study of Resin derived from Salicylaldehyde, Ethylenediamine and Formaldehyde. E-J. of Chemistry, 7(2): 564-568.

11.

Manvalan, R. and Patel, M.M. (1983). Synthesis and Study of Tercopolymers. J. Macromolecular Chem. A- 20 (9): 907-925.

12.

Masram, D.T. , Kariya, K.P. and Bhave N.S. (2007). Synthesis of Resin-I: Salicylic acid hexamethylenediamine and Formaldehyde and its ion exchange properties. Epolymers, ISSN 1618-7229: 75.

13.

Jadhao, M.M. , Paliwal, L.J. and Bhave N.S. (2005). Resin I: Synthesis and characterization of 2,2-dihydroxybiphenyl-urea-formaldehyde terpolymers , J. Appl. Polym. Sci., 96(5): 1605-1610.

14.

Jadhao, M.M. , Paliwal, L.J. and Bhave N.S. (2009). Ion-exchange properties of 2,2’-dihydroxybiphenyl-urea-formaldehyde terpolymer resins. Desalination, 247(1-3): 456-465.

15.

Gurnule, W.B. , Juneja, H.D. , Paliwal, L.J. and Kharat, R.B. (2003). Synthesis, characterization and ion-exchange properties of 4-hydroxyacetophenone, biuret and formaldehyde terpolymer resins. React. Funct. Polym . 55: 255-265.

16.

Freeman, E.S. and Carroll, B.J. (1958). The Application of Thermoanalytical Techniques to Reaction Kinetics: The Thermogravimetric Evaluation of the Kinetics of the Decomposition of Calcium Oxalate Monohydrate . Phys. Chem. 62(4): 394-397.

17.

Freeman, E.S. and Anderson, D.A. (1961). The kinetics of the thermal degradation of polystyrene and polyethylene. J. Polym . 54(159): 253-260.

18.

Sharp, J.B. and Wentworth, S.A. (1969). Kinetic analysis of thermogravimetric. Anal. Chem. 41(14): 2060- 2062.

19.

Coats, A.W. and Redfen, J.P. (2003). Kinetic parameters from thermogravimetric data. II. J. of Polym. Sc. Part B: Polymer Letters, 3(11): 917-920, Published Online: 10 Mar 2003.

20.

Ozawa, T. (1971). Kinetics of non-isothermal crystallization. Polymer 12(3): 150-158.

21.

Ozawa, T. (1986). Applicability of Friedman Plot. J. of Thermal Analysis, 31: 547-551.

22.

Joshi, R.M. and Patel, M.M. (1983). p-Hydroxybenzoic Acid-Urea-Formaldehyde Copolymers and Their Ion-Exchange Properties. J. Macromolecular Chem. 19: 705.

23.

Pal, T.K. and Kharat, R.B. (1982). Salicylic acid-biuret-trioxane terpolymer resins and their ion-exchange properties. Angewandte Macromol Chem., 173(1): 55-68. Published Online: 12 Mar 2003.

24.

Dudley, H. and Fleming, I. ( 1975). Spectroscopic Methods in Organic Chemistry, McGraw-Hill, UK.

25.

Silverstein, R.M. and Bassler, G.C. (1967). Spectrometric Identification of Organic Compounds, 2nd edn, Wiley: New York.

26.

Kemp, W. ( 1975). Organic Spectroscopy. The Macmillan Press, Hong Kong Press.

27.

Dyer, J.R. ( 1975). Application of Absorption Spectroscopy of Organic and Biological Chemistry. MIR, Moscow .

28.

Vogel, A.I. ( 1989). Textbook of Practical Organic Chemistry. Longman Scientific and Technical, UK.

29.

Jacobs, P.W. and Tompkins, F.C. ( 1955). Chemistry of Solids State. E. G. Garner Publication, London, p. 188.