Synthesis and Thermal Characterization of Novel Poly(azomethine-urethane)s Derived from Azomethine Containing Phenol and Polyphenol Species

Ismet Kaya; Mehmet Yıldırım; Ali Avcı; Musa Kamacı

Macromolecular Research, Vol.19, No.3, 286-293, March, 2011

DOI10.1007/s13233-011-0306-1 Export Citation

Synthesis and Thermal Characterization of Novel Poly(azomethine-urethane)s Derived from Azomethine Containing Phenol and Polyphenol Species

Ismet Kaya^†, Mehmet Yıldırım, Ali Avcı¹, and Musa Kamacı²

Department of Chemistry, Canakkale Onsekiz Mart University, Faculty of Sciences and Arts, 17020, Canakkale, Turkey
¹Department of Chemistry, Celal Bayar University, Faculty of Sciences and Arts, 45040, Manisa, Turkey
²Department of Chemistry, Karamano lu Mehmetbey University, Kamil Özda Science Faculty, 70100, Karaman, Turkey

E-mail:

Oligophenol-based poly(azomethine-urethane)s (PAMUs) were newly synthesized in two steps. At the first step, the prepolymers including the phenol and oligophenol based-Schiff bases were prepared by a condensation reaction of o-dianisidine with 4-hydroxybenzaldehyde/3-ethoxy-4-hydroxybenzaldehyde, and the polycondensation reactions of the corresponding Schiff bases in an aqueous alkaline media. At the second step, the PAMUs were obtained by copolymerization of the prepolymers with toluene-2,4-diisocyanate (TDI) under an argon atmosphere. The structures of the obtained compounds were confirmed by FTIR, UV-vis, 1H NMR, and 13C NMR, and size exclusion chromatography (SEC) techniques. The synthesized compounds were also characterized by TG-DTA and DSC analyses. Thermal decomposition steps at various temperatures were clarified by FTIR analyses of the degraded products. The physical changes to the synthesized PAMUs after exposing them to the thermal degradation steps are displayed.

Keywords:poly(azomethine-urethane);thermal degradation;polyurethane;oligophenol;o-dianisidine.

[References]

Yang CJ, Jenekhe SA, Chem. Mater., 6, 196 (1994)
Wang CG, Shieh S, Legoff E, Kanatzidis MG, Macromolecules, 29(9), 3147 (1996)
Grigoras M, Catanescu CO, J. Macromol. Sci.-Polym. Rev, 44, 131 (2004)
Marin L, Cozan V, Bruma M, Grigoras VC, Eur. Polym. J., 42, 1173 (2006)
Tanaka H, Shibahara Y, Sato T, Ota T, Eur. Polym. J., 2, 1525 (1993)
Sun SJ, Chang TC, Li CH, Eur. Polym. J., 29, 951 (1993)
Li CH, Chang TC, J. Polym. Sci. A: Polym. Chem., 29, 361 (1991)
Marin L, Cozan V, Bruma M, Polym. Adv. Technol., 17, 654 (2006)
Banerjee S, Saxena C, J. Polym. Sci. A: Polym. Chem., 34(17), 3565 (1996)
Gaina C, Gaina V, Sava M, High Perform. Polym., 13, 4 (2001)
Carter KR, Hedrick JL, Macromolecules, 27(12), 3426 (1994)
Issam AM, Atto AT, Sara FY, Iraq Pat., 2508 (1993)
Kaya I, Bilici A, Sack M, Synth. Met., 159, 1914 (2009)
Kaya I, Yildirim M, Avc A, Synth. Met., 160, 911 (2010)
Kaya I, Culhaoglu S, Senol D, Chin. J. Polym. Sci., 25, 461 (2007)
Kaya I, Bilici A, Gul M, Polym. Adv. Technol., 19, 1154 (2008)
Howard GT, Int. Biodeter. Biodegr., 49, 245 (2002)
Jena KK, Chattopadhyay DK, Raju KVSN, Eur. Polym. J., 43, 1825 (2007)
Chattopadhyay DK, Sreedhar B, Raju KVSN, J. Appl. Polym. Sci., 95(6), 1509 (2005)
Caki SM, Nikoli GS, Stamenkovi JV, Polym. Adv. Technol., 46, 299 (2007)
Buruiana EC, Olaru M, Simionescu BC, Eur. Polym. J., 38, 1079 (2002)
Issam AM, Ismail J, J. Appl. Polym. Sci., 100(2), 1198 (2006)
Reddy KR, Raghu AV, Jeong HM, Polym. Bull., 60(5), 609 (2008)
Tamareselvely K, Venkatarao K, Khothandaraman H, Makromol. Chem., 191, 1231 (1990)
Kaya I, Yildirim M, Kamaci M, Eur. Polym. J., 45, 1586 (2009)
Solymosi F, Rasko J, J. Catal., 63, 217 (1980)
Xiang JF, Rondonuwu FS, Kakitani Y, Fujii R, Watanabe Y, Koyama Y, Nagae H, Yamano Y, Ito M, J. Phys. Chem. B, 109(36), 17066 (2005)
Kaya I, Bilici A, J. Macromol. Sci. A, 43, 719 (2006)
Pielichowski K, Polym. J., 29, 848 (1997)
Lage LG, Kawano Y, J. Appl. Polym. Sci., 79(5), 910 (2001)
Lee HK, Ko SW, J. Appl. Polym. Sci., 50, 1269 (1993)
Grassie N, Mendoza GAP, Polym. Degrad. Stabil., 11, 359 (1985)
Day M, Cooney JD, MacKinnon M, Polym. Degrad. Stabil., 48, 341 (1995)
Zhang Y, Shang S, Zhang X, Wang D, Hourston DJ, J. Appl. Polym. Sci., 58(10), 1803 (1995)
Chattopadhyayl DK, Webster DC, Prog. Polym. Sci, 34, 1068 (2009)

[Referenced By]

[1] Yang CJ, Jenekhe SA, Chem. Mater., 6, 196 (1994)

[2] Wang CG, Shieh S, Legoff E, Kanatzidis MG, Macromolecules, 29(9), 3147 (1996)

[3] Grigoras M, Catanescu CO, J. Macromol. Sci.-Polym. Rev, 44, 131 (2004)

[4] Marin L, Cozan V, Bruma M, Grigoras VC, Eur. Polym. J., 42, 1173 (2006)

[5] Tanaka H, Shibahara Y, Sato T, Ota T, Eur. Polym. J., 2, 1525 (1993)

[6] Sun SJ, Chang TC, Li CH, Eur. Polym. J., 29, 951 (1993)

[7] Li CH, Chang TC, J. Polym. Sci. A: Polym. Chem., 29, 361 (1991)

[8] Marin L, Cozan V, Bruma M, Polym. Adv. Technol., 17, 654 (2006)

[9] Banerjee S, Saxena C, J. Polym. Sci. A: Polym. Chem., 34(17), 3565 (1996)

[10] Gaina C, Gaina V, Sava M, High Perform. Polym., 13, 4 (2001)

[11] Carter KR, Hedrick JL, Macromolecules, 27(12), 3426 (1994)

[12] Issam AM, Atto AT, Sara FY, Iraq Pat., 2508 (1993)

[13] Kaya I, Bilici A, Sack M, Synth. Met., 159, 1914 (2009)

[14] Kaya I, Yildirim M, Avc A, Synth. Met., 160, 911 (2010)

[15] Kaya I, Culhaoglu S, Senol D, Chin. J. Polym. Sci., 25, 461 (2007)

[16] Kaya I, Bilici A, Gul M, Polym. Adv. Technol., 19, 1154 (2008)

[17] Howard GT, Int. Biodeter. Biodegr., 49, 245 (2002)

[18] Jena KK, Chattopadhyay DK, Raju KVSN, Eur. Polym. J., 43, 1825 (2007)

[19] Chattopadhyay DK, Sreedhar B, Raju KVSN, J. Appl. Polym. Sci., 95(6), 1509 (2005)

[20] Caki SM, Nikoli GS, Stamenkovi JV, Polym. Adv. Technol., 46, 299 (2007)

[21] Buruiana EC, Olaru M, Simionescu BC, Eur. Polym. J., 38, 1079 (2002)

[22] Issam AM, Ismail J, J. Appl. Polym. Sci., 100(2), 1198 (2006)

[23] Reddy KR, Raghu AV, Jeong HM, Polym. Bull., 60(5), 609 (2008)

[24] Tamareselvely K, Venkatarao K, Khothandaraman H, Makromol. Chem., 191, 1231 (1990)

[25] Kaya I, Yildirim M, Kamaci M, Eur. Polym. J., 45, 1586 (2009)

[26] Solymosi F, Rasko J, J. Catal., 63, 217 (1980)

[27] Xiang JF, Rondonuwu FS, Kakitani Y, Fujii R, Watanabe Y, Koyama Y, Nagae H, Yamano Y, Ito M, J. Phys. Chem. B, 109(36), 17066 (2005)

[28] Kaya I, Bilici A, J. Macromol. Sci. A, 43, 719 (2006)

[29] Pielichowski K, Polym. J., 29, 848 (1997)

[30] Lage LG, Kawano Y, J. Appl. Polym. Sci., 79(5), 910 (2001)

[31] Lee HK, Ko SW, J. Appl. Polym. Sci., 50, 1269 (1993)

[32] Grassie N, Mendoza GAP, Polym. Degrad. Stabil., 11, 359 (1985)

[33] Day M, Cooney JD, MacKinnon M, Polym. Degrad. Stabil., 48, 341 (1995)

[34] Zhang Y, Shang S, Zhang X, Wang D, Hourston DJ, J. Appl. Polym. Sci., 58(10), 1803 (1995)

[35] Chattopadhyayl DK, Webster DC, Prog. Polym. Sci, 34, 1068 (2009)