Thermal stability and degradation of chitosan modified with phenylacetic acid

Mostafa Amin Diab; Adel Zaki El-Sonbati; Ibrahim Mohi El-dien; Dina Mohamed Diaa Bader

Korean Journal of Chemical Engineering, Vol.30, No.10, 1966-1971, October, 2013

DOI10.1007/s11814-013-0134-4 Export Citation

Thermal stability and degradation of chitosan modified with phenylacetic acid

Mostafa Amin Diab, Adel Zaki El-Sonbati^†, Ibrahim Mohi El-dien¹, and Dina Mohamed Diaa Bader

Chemistry Department, Faculty of Science, Damietta University, Damietta, Egypt
¹Chemistry Department, Faculty of Science, Port-Said University, Port-Said, Egypt

E-mail:

N-(phenylacetyl) chitosan (NPAC) polymer was synthesized by the reaction of phenylacetic acid with chitosan. The chemical structure of the formed polymer was characterized by IR and microanalysis. Thermogravimetric analysis revealed that the thermal stability of the NPAC polymer was less than that of chitosan. The products of NPAC thermal degradation were identified by the GC-MS technique. The results indicate that the mechanism of degradation of NPAC polymer is characterized by the elimination of low-molecular weight radicals. A combination of these radicals and a random scission mechanism along the backbone chain are the main source of the degradation products.

Keywords:N-(phenylacetyl) Chitosan;Thermal Stability;Mechanism of Degradation

[References]

Binsu VV, Nagarate RK, Shahi VK, Ghosh PK, Reac.Funct. Polym., 66, 1619 (2006)
Britto C, Assis OBG, Carbohydr. Polym., 69, 305 (2006)
Prashanth HKV, Tharanathan RN, Trends Food Sci. Technol., 18, 117 (2007)
Crinic G, Prog. Polym. Sci., 30, 38 (2005)
Agullo E, Rodriquez MS, Ramos V, Macromol. Biosci., 3, 521 (2003)
Sashiwa H, Aiba SI, Prog. Polym. Sci., 29, 887 (2004)
Chenite A, Chaput C, Wang D, Cambes C, Buschmann MD, Hoemann CD, Leroax JC, Atkinson BL, Binette F, Selmani A, Biomat., 21, 2155 (2000)
Hsu SH, Whu SW, Tsai CL, Wu YH, Chen HW, Hsieh KH, J. Polym. Res., 11, 141 (2004)
Huang M, Khor E, Lim LY, Pharm. Res., 21, 344 (2004)
Agnihotri SA, Mallikarjuna NN, Aminabhavi TM, J. Cont. Release., 100, 28 (2004)
Yang ZK, Yuan Y, J. Appl. Polym. Sci., 82(8), 1838 (2001)
Kurkuri MD, Kulkarni AR, Aminabhavi TM, J. Appl. Polym. Sci., 86(2), 526 (2002)
Agnihotri SA, Kulkarni VD, Kulkarni AR, Aminabhavi TM, J. Appl. Polym. Sci., 102(4), 3255 (2006)
Bihari-Varag M, Sepulcher M, Moczar CE, J. Therm. Anal., 7, 675 (1975)
Austin PR, US Patent, 3,879,377 (1975)
Tirkistani FAA, Polym. Degrad. Stab., 60, 67 (1998)
Tirkistani FAA, Polym. Degrad. Stab., 61, 161 (1998)
Sashiwa H, Yamamorin N, Ichinose Y, Sunamoto J, Aiba S, Biomacromolecules., 5, 1250 (2003)
Sashiwa H, Kawasaki N, Nakayama A, Muraki E, Yamamoto N, Aiba S, Biomacromolecules, 3(5), 1126 (2002)
Diab MA, El-Sonbati AZ, Bader DMD, Spectrochim. Acta A., 79, 1057 (2011)
Diab MA, El-Sonbati AZ, Bader DMD, Zoromba MS, J. Polym. Environ., 20, 29 (2012)
Diab MA, El-Sonbati AZ, El-Halawany MM, Bader DMD, Open J. Polym. Chem., 2, 14 (2012)
Fernandez-Megia E, Novoa-Carbollal R, Quinoa E, Riguera R, Carbohyd. Polym., 61, 155 (2005)
Lavertu M, Xia Z, Serreqi AN, Berrada M, Radrigues A, Wang D, J. Pharm. Biomed. Anal., 32, 1149 (2003)
Rinaudo M, Milas M, Dung PL, Int. J. Biol. Macromol., 15, 281 (1993)
Muzzarelli RAA, Ferrero A, Pizzoli M, Talanta., 19, 122 (1972)
Brugnerotto J, Lizardi J, Goycoolea FM, Arguelles-Monal W, Desbrieres J, Rinaudo M, Polymer, 42(8), 3569 (2001)

[Referenced By]

[1] Binsu VV, Nagarate RK, Shahi VK, Ghosh PK, Reac.Funct. Polym., 66, 1619 (2006)

[2] Britto C, Assis OBG, Carbohydr. Polym., 69, 305 (2006)

[3] Prashanth HKV, Tharanathan RN, Trends Food Sci. Technol., 18, 117 (2007)

[4] Crinic G, Prog. Polym. Sci., 30, 38 (2005)

[5] Agullo E, Rodriquez MS, Ramos V, Macromol. Biosci., 3, 521 (2003)

[6] Sashiwa H, Aiba SI, Prog. Polym. Sci., 29, 887 (2004)

[7] Chenite A, Chaput C, Wang D, Cambes C, Buschmann MD, Hoemann CD, Leroax JC, Atkinson BL, Binette F, Selmani A, Biomat., 21, 2155 (2000)

[8] Hsu SH, Whu SW, Tsai CL, Wu YH, Chen HW, Hsieh KH, J. Polym. Res., 11, 141 (2004)

[9] Huang M, Khor E, Lim LY, Pharm. Res., 21, 344 (2004)

[10] Agnihotri SA, Mallikarjuna NN, Aminabhavi TM, J. Cont. Release., 100, 28 (2004)

[11] Yang ZK, Yuan Y, J. Appl. Polym. Sci., 82(8), 1838 (2001)

[12] Kurkuri MD, Kulkarni AR, Aminabhavi TM, J. Appl. Polym. Sci., 86(2), 526 (2002)

[13] Agnihotri SA, Kulkarni VD, Kulkarni AR, Aminabhavi TM, J. Appl. Polym. Sci., 102(4), 3255 (2006)

[14] Bihari-Varag M, Sepulcher M, Moczar CE, J. Therm. Anal., 7, 675 (1975)

[15] Austin PR, US Patent, 3,879,377 (1975)

[16] Tirkistani FAA, Polym. Degrad. Stab., 60, 67 (1998)

[17] Tirkistani FAA, Polym. Degrad. Stab., 61, 161 (1998)

[18] Sashiwa H, Yamamorin N, Ichinose Y, Sunamoto J, Aiba S, Biomacromolecules., 5, 1250 (2003)

[19] Sashiwa H, Kawasaki N, Nakayama A, Muraki E, Yamamoto N, Aiba S, Biomacromolecules, 3(5), 1126 (2002)

[20] Diab MA, El-Sonbati AZ, Bader DMD, Spectrochim. Acta A., 79, 1057 (2011)

[21] Diab MA, El-Sonbati AZ, Bader DMD, Zoromba MS, J. Polym. Environ., 20, 29 (2012)

[22] Diab MA, El-Sonbati AZ, El-Halawany MM, Bader DMD, Open J. Polym. Chem., 2, 14 (2012)

[23] Fernandez-Megia E, Novoa-Carbollal R, Quinoa E, Riguera R, Carbohyd. Polym., 61, 155 (2005)

[24] Lavertu M, Xia Z, Serreqi AN, Berrada M, Radrigues A, Wang D, J. Pharm. Biomed. Anal., 32, 1149 (2003)

[25] Rinaudo M, Milas M, Dung PL, Int. J. Biol. Macromol., 15, 281 (1993)

[26] Muzzarelli RAA, Ferrero A, Pizzoli M, Talanta., 19, 122 (1972)

[27] Brugnerotto J, Lizardi J, Goycoolea FM, Arguelles-Monal W, Desbrieres J, Rinaudo M, Polymer, 42(8), 3569 (2001)