Abstract
Three procedures for the chemical oxidative polymerization of diphenylamine, namely, in solutions of sulfuric acid, in an H2SO4-tert-butanol mixture, and via the interfacial process, are considered. It was shown that the highest molecular mass products are formed by the interfacial process. Oxidative hydrolysis and chain termination reactions predominate in a homogeneous medium. The effects of polymerization conditions, such as the concentration of reagents, their ratio, and the reaction temperature, on the yield and molecular-mass characteristics of polydiphenylamine were studied. The structure of reaction products was investigated by UV spectroscopy. It was demonstrated that, even when ammonium persulfate is in excess, the degree of oxidation of polydiphenylamine is rather small and chain propagation proceeds as a C-C rather than N-C addition as in the case of aniline.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. Malinauskas, Polymer 42, 3957 (2001).
A. G. McDiarmid, Synth. Met. 125, 11 (2002).
C. R. Martin, Chem. Mater. 8, 1739 (1996).
M. Delvaux, J. Duchet, P.-Y. Stavaux, et al., Synth. Met. 113, 275 (2000).
Q. Wu, Z. Xue, Z. Qi, and F. Wang, Polymer 41, 2029 (2000).
M. Kryszewski, Synth. Met. 109, 47 (2000).
A. V. Orlov, S. G. Kiseleva, G. P. Karpacheva, et al., J. Polym. Sci. 89, 1379 (2003).
A. V. Orlov, O. Yu. Yurchenko, S. G. Kiseleva, et al., Vysokomol. Soedin., Ser. A 43, 890 (2001) [Polymer Science, Ser. A 43, 572 (2001)].
T.-C. Wen, C. Sivakumar, and A. Gopalan, Spectrochim. Acta, Part A 58, 167 (2002).
P. A. Kilmartin and G. A. Wright, Synth. Met. 104, 145 (1999).
L. H. C. Mattoso, L. G. Paterno, S. P. Campana, and O. N. Oliveria, Jr., Synth. Met. 84, 123 (1997).
L. H. C. Mattoso and L. O. S. Bulhoes, Synth. Met. 52, 171 (1992).
A. H. Kwon, J. A. Conklin, M. Makhinson, and R. B. Kaner, Synth. Met. 84, 95 (1997).
X.-H. Wang, L.-X. Wang, X.-B. Jing, and F.-S. Wang, Synth. Met. 69, 149 (1995).
X.-H. Wang, J. Li, L.-X. Wang, et al., Synth. Met. 69, 147 (1995).
E. V. Strounina, A. P. Leon, and G. G. Kane-Maguire, Synth. Met. 106, 129 (1999).
H. S. O. Chan, S. C. Ng, L. S. Leong, and K. L. Tan, Synth. Met. 68, 199 (1995).
F. Cataldo, Eur. Polym. J. 32, 43 (1996).
D. Goncalves, R. C. Faria, M. Yonashiro, and L. O. S. Bulhoes, J. Electroanal. Chem. 487, 90 (2000).
U. Hayat, P. N. Bartlett, G. H. Dodd, and J. Barker, J. Electroanal. Chem. 220, 287 (1987).
J. Guay and H. Dao Le, J. Electroanal. Chem. 274, 135 (1989).
Yu. V. Karyakin and I. I. Angelov, Pure Chemicals (Khimiya, Moscow, 1974) [in Russian].
A. Weissberger, E. Proskauer, T. Riddick, and E. Toops, Organic Solvents. Physical Properties and Methods of Purification (Wiley, New York, 1955; Inostrannaya Literatura, Moscow, 1958).
B. D. Berezin and D. B. Berezin, Modern Organic Chemistry: A Manual for Institutes (Vysshaya Shkola, Moscow, 1999) [in Russian].
F. Lux, Polymer 35, 2915 (1994).
P. N. Adams, P. J. Laughlin, A. P. Monkman, and A. M. Kenwright, Polymer 37, 3411 (1996).
P. N. Adams, P. J. Laughlin, and A. P. Monkman, Synth. Met. 76, 157 (1996).
J. Stejskal, A. Riede, D. Hlavata, et al., Synth. Met. 96, 55 (1998).
P. N. Adams and A. P. Monkman, Synth. Met. 87, 165 (1997).
Author information
Authors and Affiliations
Additional information
Original Russian Text © A.V. Orlov, S.Zh. Ozkan, G.N. Bondarenko, G.P. Karpacheva, 2006, published in Vysokomolekulyarnye Soedineniya, Ser. B, 2006, Vol. 48, No. 1, pp. 126–133.
Rights and permissions
About this article
Cite this article
Orlov, A.V., Ozkan, S.Z., Bondarenko, G.N. et al. Oxidative polymerization of diphenylamine: Synthesis and structure of polymers. Polym. Sci. Ser. B 48, 5–10 (2006). https://doi.org/10.1134/S1560090406010027
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1134/S1560090406010027