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A Facile Synthesis of Poly(acrylanilide-co-acrylic Acid)
Corresponding Author(s) : Shufen Zhang
Asian Journal of Chemistry,
Vol. 25 No. 6 (2013): Vol 25 Issue 6
Abstract
A range of poly(acrylanilide-co-acrylic acid) was synthesized through a facile one-pot condensation of poly(acrylic acid) with aromatic amines. Thionyl chloride was added in a stepwise manner to N,N-dimethyl acetamide and poly(acryloyl chloride) need not be isolated during the reaction. Compared with conventional methods, the condensation of poly(acryloyl chloride) with aromatic amines could perform without the addition of other bases (such as triethylamine, pyridine, etc.). Regardless of electron-withdrawing or electron-donating groups the aromatic amines contain, the reaction was carried out smoothly. Different molar ratios of poly(acrylic acid) (acrylic acid units) to aromatic amines were investigated and moderate yields were obtained. The products were characterized by nuclear magnetic resonance spectroscopy and Fourier-transform infrared spectroscopy.
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- I. Gourevich, H. Pham, J.E.N. Jonkman and E. Kumacheva,Chem. Mater., 16, 1472 (2004).
- F. Sartain, X.P. Yang and C.R. Lowe, Anal. Chem., 78, 5664 (2006).
- V.A. Sethuraman, K. Na and Y.H. Bae, Biomacromolecules, 7, 64 (2006).
- S.Q. Li, E. Davis, J. Anderson, Q. Lin and Q. Wang, Biomacromolecules, 10, 113 (2009).
- Y. Okamoto, T. Kaku and R. Shundo, Pure. Appl. Chem., 68, 1417 (1996).
- C. Renner, J. Piehler and T. Schrader, J. Am. Chem. Soc., 128, 620 (2006).
- S.W. Hong and W.H. Jo, Polymer, 49, 4180 (2008).
- H. Hosseinzadeh and M. Sadeghi, Asian J. Chem., 24, 85 (2012).
- A. Cutivet, C. Schembri, J. Kovensky and K. Haupt, J. Am. Chem. Soc., 131, 14699 (2009).
- G.U. Akkus and C. Cebeci, J. Incl. Phenom. Macrocycl. Chem., 62, 303 (2008).
- S.K. Han, K. Na and Y.H. Bae, Colloids Surf. A, 214, 49 (2003).
- H. Hakala, V. Mukkala, T. Sutela and J. Hovinen, Org. Biomol. Chem., 4, 1383 (2006).
- M. Obata, M. Morita, K. Nakase, K. Mitsuo, K. Asai, S. Hirohara and S. Yano, J. Polym. Sci. A, 45, 2876 (2007).
- N. Tirelli, U. W. Suter, A. Altomare, R. Solaro, F. Ciardelli, S. Follonier, C. Bosshard and P. Günter, Macromolecules, 31, 2152 (1998).
- N. Tirelli,A. Altomare, R. Solaro, F. Ciardelli, S. Follonier, C. Bosshard and P. Günter, Polymer, 41, 415 (2000).
- L.F. Campo, F.S. Rodembusch and V. Stefani, J. Appl. Polym. Sci., 99, 2109 (2006).
- E.C. Buruiana, T. Buruiana and L. Hahui, J. Photochem. Photobiol. A, 189, 65 (2007).
- R.J. Cvetovich and L. DiMichele, Org. Process. Res. Dev., 10, 944 (2006).
- Y.F. Sun, D.F. Zhao and H.S. Freeman, Dyes Pigm., 74, 608 (2007).
- C. Bunyakan and D. Hunkeler, Polymer, 40, 6213 (1999).
- C. Bunyakan and D. Hunkeler, Polymer, 40, 6225 (1999).
- J.S. Shih and T.E. Smith, WO Patent 9319098 (1993)
References
I. Gourevich, H. Pham, J.E.N. Jonkman and E. Kumacheva,Chem. Mater., 16, 1472 (2004).
F. Sartain, X.P. Yang and C.R. Lowe, Anal. Chem., 78, 5664 (2006).
V.A. Sethuraman, K. Na and Y.H. Bae, Biomacromolecules, 7, 64 (2006).
S.Q. Li, E. Davis, J. Anderson, Q. Lin and Q. Wang, Biomacromolecules, 10, 113 (2009).
Y. Okamoto, T. Kaku and R. Shundo, Pure. Appl. Chem., 68, 1417 (1996).
C. Renner, J. Piehler and T. Schrader, J. Am. Chem. Soc., 128, 620 (2006).
S.W. Hong and W.H. Jo, Polymer, 49, 4180 (2008).
H. Hosseinzadeh and M. Sadeghi, Asian J. Chem., 24, 85 (2012).
A. Cutivet, C. Schembri, J. Kovensky and K. Haupt, J. Am. Chem. Soc., 131, 14699 (2009).
G.U. Akkus and C. Cebeci, J. Incl. Phenom. Macrocycl. Chem., 62, 303 (2008).
S.K. Han, K. Na and Y.H. Bae, Colloids Surf. A, 214, 49 (2003).
H. Hakala, V. Mukkala, T. Sutela and J. Hovinen, Org. Biomol. Chem., 4, 1383 (2006).
M. Obata, M. Morita, K. Nakase, K. Mitsuo, K. Asai, S. Hirohara and S. Yano, J. Polym. Sci. A, 45, 2876 (2007).
N. Tirelli, U. W. Suter, A. Altomare, R. Solaro, F. Ciardelli, S. Follonier, C. Bosshard and P. Günter, Macromolecules, 31, 2152 (1998).
N. Tirelli,A. Altomare, R. Solaro, F. Ciardelli, S. Follonier, C. Bosshard and P. Günter, Polymer, 41, 415 (2000).
L.F. Campo, F.S. Rodembusch and V. Stefani, J. Appl. Polym. Sci., 99, 2109 (2006).
E.C. Buruiana, T. Buruiana and L. Hahui, J. Photochem. Photobiol. A, 189, 65 (2007).
R.J. Cvetovich and L. DiMichele, Org. Process. Res. Dev., 10, 944 (2006).
Y.F. Sun, D.F. Zhao and H.S. Freeman, Dyes Pigm., 74, 608 (2007).
C. Bunyakan and D. Hunkeler, Polymer, 40, 6213 (1999).
C. Bunyakan and D. Hunkeler, Polymer, 40, 6225 (1999).
J.S. Shih and T.E. Smith, WO Patent 9319098 (1993)