Effect of functional groups on the thermal degradation of phosphorus- and phosphorus/nitrogen-containing functional polymers
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Abstract
In the present study the thermal behavior of phosphorus- and phosphorus/nitrogen-containing functional polymers was studied. The polymers were synthesized via oxidative chlorophosphorylation reaction of butadiene rubber and were subsequently subjected to hydrolysis, aminolysis and/or alcoholysis in order to introduce appropriate functionalities. The successful modifications of the polymer and presences of the respective functional groups were determined using Fourier transform infrared spectroscopy. It was found that the product of hydrolysis of the modified butadiene rubber contains acidic groups in its structure while the products of aminolysis and alcoholysis contain both acidic and amine and/or alcohol-derived moieties. The kinetic analyses of the thermal decomposition reaction were evaluated using thermogravimetric analysis and subsequently Friedman and Ozawa–Flynn–Wall methods revealing three-stage degradation process. Calorimetric measurements were performed for the studied polymers, and mass spectrometric analyses were used to identify the decomposition products for phosphorus-containing polymer. The overall results allowed to reveal the influence of the attached phosphorus- and phosphorus/nitrogen-containing functional groups to the thermal degradation of the cross-linked polymers.
Keywords
Butadiene rubber Functional groups Thermal behavior Kinetic parameters of degradationNotes
Acknowledgements
The authors would like to thank German Academic Exchange Service (DAAD) and German Research Center for Environmental Health, Helmholtz Zentrum München, Joint Mass Spectrometry Centre, Cooperation Group “Comprehensive Molecular Analytics” for financial support and work statement of the research. Part of research was done in the group of prof. Szczepan Zapotoczny (Faculty of Chemistry, Jagiellonian University) under Erasmus Mundus Electra program. Authors would like to thank Gülcin Abbaszade as well.
Supplementary material
References
- 1.Lu J, Toy PH. Organic polymer supports for synthesis and for reagent and catalyst immobilization. Chem Rev. 2009;109:815–38.CrossRefGoogle Scholar
- 2.Hartlieb M, Kempe K, Schubert US. Covalently cross-linked poly(2-oxazoline) materials for biomedical applications—from hydrogels to self-assembled and templated structures. J Mater Chem B. 2015;3:526–38.CrossRefGoogle Scholar
- 3.Mane S. Functional polymers: a review. Can Chem Trans. 2016;4:316–27.Google Scholar
- 4.Akelah A, Moet A. Functionalized polymers and their application. 1st ed. London: Chapman and Hall; 1990.Google Scholar
- 5.Frechet JM. Functional polymers: from plastic electronics to polymer-assisted therapeutics. Prog Polym Sci. 2005;30:844–57.CrossRefGoogle Scholar
- 6.Zhu X, Alexandratos SA. Development of a new ion-exchange/coordinating phosphate ligand for the sorption of U(VI) and trivalent ions from phosphoric acid solutions. Chem Eng Sci. 2015;127:126–32.CrossRefGoogle Scholar
- 7.Monge S, David G. Phosphorus-based polymers: from synthesis to applications. London: Burlington House; 2014.CrossRefGoogle Scholar
- 8.Carpenter YY, Baumgartner T. Reference module in chemistry. Mol Sci Chem Eng Phosphorus Contain Polym. 2013;1:893–932.Google Scholar
- 9.Floch PL. Phosphaalkene, phosphoryl and phosphinine ligands: new tools in coordination chemistry and catalysis. Coord Chem Rev. 2006;250:627–81.CrossRefGoogle Scholar
- 10.Hamed F, Biji P. A novel polymer containing phosphorus–nitrogen ligands for stabilization of palladium nanoparticles: an efficient and recyclable catalyst for Suzuki and Sonogashira reactions in neat water. Dalton Trans. 2015;44:14293–303.CrossRefGoogle Scholar
- 11.Buchmeiser MR. Polymeric materials in organic synthesis and catalysis. Berlin: Wiley; 2006.Google Scholar
- 12.Dorfner K. Ion exchangers. Berlin: de Gruyter; 1991.CrossRefGoogle Scholar
- 13.Zagorodni AA. Ion exchange materials: properties and applications. Amsterdam: Elsevier; 2006.Google Scholar
- 14.Acton QA. Ion exchange resins—advances in research and application. Atlanta: Scholarly Editions; 2013.Google Scholar
- 15.Helfferich F. Ion exchange. New York: Mc.Graw-Hill; 1962.Google Scholar
- 16.Iditoiu C, Segal E, Cesaro A. Kinetics of non-isothermal behaviour of synthetic cationites with low acidity. J Therm Anal Calorim. 1999;56:407–17.CrossRefGoogle Scholar
- 17.Chambre D, Iditoiu C, Segal E, Cesaro A. The study of non-isothermal degradation of acrylic ion-exchange resins. J Therm Anal Calorim. 2005;82:803–11.CrossRefGoogle Scholar
- 18.Soykan C, Coskun R, Delibas A. Thermodegradation of poly(4-vinylpyridine-co-crotonic acid-co-divinylbenzene) and N-oxide derivatives. Thermochim Acta. 2007;456:152–7.CrossRefGoogle Scholar
- 19.Riqueza EC, de Aguiar AP, de Aguiar MR, de Santa Maria LC. Thermogravimetric study of some crosslinked copolymers based on poly(acrylonitrile-co-divinylbenzene). Thermochim Acta. 2007;456:128–33.CrossRefGoogle Scholar
- 20.Bunia I, Cascaval CN, Rosu D, Ciobanu C, Popa M. Thermal degradation of some crosslinked acrylic copolymers functionalized as ion exchangers. Polym Degrad Stab. 2000;70:205–15.CrossRefGoogle Scholar
- 21.Vlad CD, Dinu MV, Dragan S. Thermogravimetric analysis of some crosslinked acrylamide copolymers and ion exchangers. Polym Degrad Stab. 2003;79:153–9.CrossRefGoogle Scholar
- 22.Matsuda M, Funabashi K, Nishi T, Yusa H, Kikuchi M. Decomposition of ion exchange resins by pyrolysis. Nucl Technol. 1986;75:187–93.CrossRefGoogle Scholar
- 23.Matsuda M, Funabashi K, Nishi T, Yusa H. Influence of functional sulfonic acid group on pyrolysis characteristics for cation exchange resin. J Nucl Sci Technol. 1987;24:124–8.CrossRefGoogle Scholar
- 24.Yang HC, Lee MW, Hwang HS, Moon JK, Chung DY. Study on thermal decomposition and oxidation kinetics of cation exchange resins using non-isothermal TG analysis. J Therm Anal Calorim. 2014;118:1073–83.CrossRefGoogle Scholar
- 25.de Santa Maria LC, Souza AV, Santos FR, Rubenich MS, Ferreira DJ, Rita MP. Thermogravimetric and spectrometric characterizations of poly(styrene-co-divinylbenzene) containing phosphinic and phosphonic acid groups. Polym Eng Sci. 2008;48:1897–900.CrossRefGoogle Scholar
- 26.Alosmanov RM, Azizov AA, Magerramov AM. NMR spectroscopic study of phosphorus-containing polymer sorbent. Russ J General Chem. 2011;81:1477–9.CrossRefGoogle Scholar
- 27.Jalbani N, Yilmaz E, Alosmanov RM, Soylak M. Solid-phase extraction of copper and zinc in water samples using diethylamine-modified phosphorus-containing polymer. Desalt Water Treat. 2016;57:2834–42.CrossRefGoogle Scholar
- 28.Soylak M, Khan M, Alosmanov RM, Shah J, Jan MR. Solid phase extraction of uranium(VI) on phosphorus-containing polymer grafted 4-aminoantipyrine. Radioanal Nucl Chem. 2016;308:955–63.CrossRefGoogle Scholar
- 29.Yilmaz E, Alosmanov RM, Soylak M. Magnetic solid phase extraction of lead(II) and cadmium(II) on a magnetic phosphorus-containing polymer (M-PhCP) for their microsampling flame atomic absorption spectrometric determinations. RSC Adv. 2015;5:33801.CrossRefGoogle Scholar
- 30.Alosmanov RM, Azizov AA. Sorption isotherms of Nickel(II), Cobalt(II), Mercury(II), and Lead(II) ions on a phosphorus-containing polymeric sorbent. Russ J Inorg Chem. 2012;57:303–5.CrossRefGoogle Scholar
- 31.Alosmanov RM, Hajiyeva HF, Azizov AA, Garibov AA, Maharramov AM, Bunyad-Zadeh IA. Equilibrium particularities of phenol sorption from aqueous solutions onto phosphorus containing sorbent. Mater Res Innov. 2010;14:169–72.CrossRefGoogle Scholar
- 32.Shagidullin RR, Chernova AV, Vinogradova VS, Mukhametov FS. Atlas of IR spectra of organophosphorus compounds. Dordrecht: Springer; 1990.CrossRefGoogle Scholar
- 33.Silverstein RM, Bassler GC, Morril TC. Spectrometric identification of organic compounds. New York: Wiley; 1980.Google Scholar
- 34.KuptsovAH, ZhizhinGN. Handbook of fourier transform raman and infrared spectra of polymers. Technosfera. 2013 (in russian).Google Scholar
- 35.Burescu AI, Sava I, Bruma M, Lisa G. Study of the thermal decomposition of some azopolyimides. High Perform Polym. 2014;26:81–8.CrossRefGoogle Scholar
- 36.Suflet DM, Chitanu GC, Popa VI. Phosphorylation of polysaccharides: new results on synthesis and characterisation of phosphorylated cellulose. React Funct Polym. 2006;66:1240–9.CrossRefGoogle Scholar
- 37.Osman EM, Khalil AA, El-Shrbini MH, Reda LM, Shaaban AF. Characterization and evaluation of phosphorus/nitrogen-containing polymer as a durable flame retardant for cotton fabrics. J Appl Chem Sci Int. 2015;3:39–52.Google Scholar
- 38.Ozawa TA. A new method of analyzing thermogravimetric data. Bull Chem Soc Jpn. 1965;38:1881–6.CrossRefGoogle Scholar
- 39.Flynn JH, Wall LA. A quick direct method for the determination of activation energy from thermogravimetric data. J Polym Sci C Polym Lett. 1966;4:323–8.CrossRefGoogle Scholar
- 40.Popescu C. Integral method to analyse the kinetics of heterogeneous reactions under non isothermal conditions. A variant on the Ozawa–Flynn–Wall method. Thermochim Acta. 1996;285:309–23.CrossRefGoogle Scholar
- 41.Friedman HL. Kinetics of thermal degradation of char-forming plastics from thermogravimetry. Application to a phenolic plastics. J Polym Sci C. 1965;6:183–95.CrossRefGoogle Scholar
- 42.Tudorachi N, Chiriac AP, Neamtu I, Nistor MT, Lisa G. Synthesis and thermal analysis of a magnetic composite by thermogravimetry coupled to fourier transform infrared spectroscopy and mass spectrometry. Ind Eng Chem Res. 2012;51:335–44.CrossRefGoogle Scholar
- 43.Tudorachi N, Bunia I. Synthesis and thermal investigation by TG–FTIR–MS analysis of some functionalized acrylic copolymers and magnetic composites with Fe3O4. J Anal App Pyrolysis. 2015;116:190–201.CrossRefGoogle Scholar
- 44.Maciejewska M. Thermal properties of TRIM–GMA copolymers with pendant amine groups. J Therm Anal Calorim. 2016;126:1777–85.CrossRefGoogle Scholar
- 45.Podkoscielna B, Lipke A, Majdan M, Gawdzik B, Bartnicki A. Thermal and photoluminescence analysis of a methacrylic diester derivative of naphthalene-2,7-diol. J Therm Anal Calorim. 2016;126:161–70.CrossRefGoogle Scholar
- 46.Worzakowska M. TG/DSC/FTIR/QMS studies on the oxidative decomposition of terpene acrylate homopolymers. J Therm Anal Calorim. 2017;127:2025–35.CrossRefGoogle Scholar