말단 수산화기를 가진 폴리락타이드와 이미다졸로 블록된 이소시아네이트를 이용한 폴리우레탄 바이오접착제의 합성 및 물성 평가

Tengfei Shen; Yingjuan Sun; Chunfeng Sun; Mangeng Lu

Polymer(Korea), Vol.37, No.2, 232-239, March, 2013

Preparation and Characterization of Polyurethane Bioadhesive from Hydroxyl-terminated Polylactide and Imidazole-blocked Isocyanate

Tengfei Shen^{1, 2, †}, Yingjuan Sun¹, Chunfeng Sun¹, and Mangeng Lu²

¹Department of Environmental Engineering, North China Institute of Science and Technology, PO Box 206, Yanjiao Beijing 101601, P. R. China
²Guangzhou Institute of Chemistry, Graduate University of Chinese Academy of Sciences, Guangzhou 510650, P. R. China

E-mail:

A series of novel imidazole-blocked diisocyanate bioadhesives (IBAs) were synthesized from reaction of toluene 2, 4-diisocyanate (TDI), isophorone diisocyanate (IPDI), hydroxyl-terminated polylactide (HO-PLA-OH), 1,1,1-trimethylolpropane (TMP), and imidazole. Synthesis of IBAs was confirmed by Fourier transform infrared spectroscopy (FTIR) and gel permeation chromatography (GPC). Differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA) revealed that the TDI-based IBA had lower thermal dissociation temperature and a faster deblocking rate than IBA based on IPDI. Hydroxyl-terminated polyurethane (HPU) was introduced to study the adhesive effect of the synthesized IBAs. Improvement on elastic modulus, tensile strength and water resistance of IBA-modified HPU in comparison with neat HPU suggested the good adhesive effect of IBA due to the strong chemical reaction between released NCO groups from IBA and hydroxyl groups from HPU.

Keywords:polyurethane adhesive;biodegradable;blocked isocyanate;hydroxyl-terminated polylactide.

[References]

Zhou J, Zhang XY, Dai JB, Li JP, J. Macromol. Sci.A: Pure Appl. Chem., 49, 890 (2012)
Awkal M, Jonquieres A, Clement R, Lochon P, Eur.Polym. J., 42, 1313 (2006)
Bahattab MA, Garcia-Pacios V, Donate-Robles J, Martin-Martinez JM, J. Adhes. Sci. Technol., 26, 303 (2012)
Peng ZY, Chen FG, Int. J. Polym. Mater., 60, 674 (2011)
Nasar AS, Raghavan A, Kumar VS, J. Macromol. Sci. A:Pure Appl. Chem., 42, 309 (2005)
Yeganeh H, Jamshidi S, Talemi PH, Eur. Polym. J., 42, 1743 (2006)
Wicks DA, Wicks ZW, Prog. Org. Coat., 36, 148 (1999)
Wicks DA, Wicks ZW, Prog. Org. Coat., 41, 1 (2001)
Oertel G, Polyurethanes, Carl Hanser Verlag, Munich (1993)
Xavier T, Didier B, Lan T, Eur. Polym. J., 36, 1745 (2000)
Schmitt F, Wenning A, Weiss JV, Prog. Org. Coat., 34, 227 (1997)
Wicks DA, Yeske PE, Prog. Org. Coat., 30, 265 (1997)
Sankar G, Nasar AS, Eur. Polym. J., 45, 911 (2009)
Choi EM, Shin KS, Hwang TS, Macromol. Res., 18(6), 577 (2010)
Desai SD, Emanuel AL, Sinha VK, Int. J. Polym.Mater., 53, 1061 (2004)
Yin LG, Liu YL, Ke Z, Yin JH, Eur. Polym. J., 45, 191 (2009)
Kothandaraman H, Nasar AS, Polymer., 34, 610 (1993)
Ahmad I, Zaidi H, Hussain R, Munir A, Polym. Int., 56, 1521 (2007)
Shen TF, Zhou DW, Liang LY, Zheng J, Lan YX, Lu MG, J. Appl. Polym. Sci., 122(2), 748 (2011)
Subramani S, Cheong IW, Kim JH, Prog. Org. Coat., 51, 329 (2004)
Lee JM, Subramani S, Lee YS, Kim JH, Macromol. Res., 13(5), 427 (2005)
Karchin A, Simonovsky FI, Ratner BD, Sanders JE, Acta. Biomater., 7, 3277 (2011)
Ryszkowska JL, Auguscik M, Sheikh A, Boccaccini AR, Compos. Sci. Technol., 70, 1894 (2010)
Park BJ, Kwon BJ, Kang JK, Lee MH, Han I, Kim JK, Park JC, Macromol. Res., 19(6), 537 (2011)
Sun XK, Gao H, Wu GL, Wang YN, Fan YG, Ma JB, Int. J. Pharm., 412, 52 (2011)
Oertel G, Polyurethane Handbook, Hanser, New York (1985)
Thomas P, Polyurethanes, Vol III, 2ed., Wiley & Sons, London (1998)
Ranjbar Z, Montazeri S, Mohammad M, Nayini R, Jannesari A, Prog. Org. Coat., 69, 426 (2010)
Seymour RW, Cooper SL, Macromolecules., 6, 48 (1973)
Gedan-Smolka M, Haussler L, Fischer D, Thermochim. Acta, 351(1-2), 95 (2000)
Woods G, The ICI Polyurethane Book, 2nd ed., Wiley & Sons, New York (1990)
Nasar AS, Subramani S, Radhakrishnan G, Polym. Int., 48, 614 (1999)

[Referenced By]

[1] Zhou J, Zhang XY, Dai JB, Li JP, J. Macromol. Sci.A: Pure Appl. Chem., 49, 890 (2012)

[2] Awkal M, Jonquieres A, Clement R, Lochon P, Eur.Polym. J., 42, 1313 (2006)

[3] Bahattab MA, Garcia-Pacios V, Donate-Robles J, Martin-Martinez JM, J. Adhes. Sci. Technol., 26, 303 (2012)

[4] Peng ZY, Chen FG, Int. J. Polym. Mater., 60, 674 (2011)

[5] Nasar AS, Raghavan A, Kumar VS, J. Macromol. Sci. A:Pure Appl. Chem., 42, 309 (2005)

[6] Yeganeh H, Jamshidi S, Talemi PH, Eur. Polym. J., 42, 1743 (2006)

[7] Wicks DA, Wicks ZW, Prog. Org. Coat., 36, 148 (1999)

[8] Wicks DA, Wicks ZW, Prog. Org. Coat., 41, 1 (2001)

[9] Oertel G, Polyurethanes, Carl Hanser Verlag, Munich (1993)

[10] Xavier T, Didier B, Lan T, Eur. Polym. J., 36, 1745 (2000)

[11] Schmitt F, Wenning A, Weiss JV, Prog. Org. Coat., 34, 227 (1997)

[12] Wicks DA, Yeske PE, Prog. Org. Coat., 30, 265 (1997)

[13] Sankar G, Nasar AS, Eur. Polym. J., 45, 911 (2009)

[14] Choi EM, Shin KS, Hwang TS, Macromol. Res., 18(6), 577 (2010)

[15] Desai SD, Emanuel AL, Sinha VK, Int. J. Polym.Mater., 53, 1061 (2004)

[16] Yin LG, Liu YL, Ke Z, Yin JH, Eur. Polym. J., 45, 191 (2009)

[17] Kothandaraman H, Nasar AS, Polymer., 34, 610 (1993)

[18] Ahmad I, Zaidi H, Hussain R, Munir A, Polym. Int., 56, 1521 (2007)

[19] Shen TF, Zhou DW, Liang LY, Zheng J, Lan YX, Lu MG, J. Appl. Polym. Sci., 122(2), 748 (2011)

[20] Subramani S, Cheong IW, Kim JH, Prog. Org. Coat., 51, 329 (2004)

[21] Lee JM, Subramani S, Lee YS, Kim JH, Macromol. Res., 13(5), 427 (2005)

[22] Karchin A, Simonovsky FI, Ratner BD, Sanders JE, Acta. Biomater., 7, 3277 (2011)

[23] Ryszkowska JL, Auguscik M, Sheikh A, Boccaccini AR, Compos. Sci. Technol., 70, 1894 (2010)

[24] Park BJ, Kwon BJ, Kang JK, Lee MH, Han I, Kim JK, Park JC, Macromol. Res., 19(6), 537 (2011)

[25] Sun XK, Gao H, Wu GL, Wang YN, Fan YG, Ma JB, Int. J. Pharm., 412, 52 (2011)

[26] Oertel G, Polyurethane Handbook, Hanser, New York (1985)

[27] Thomas P, Polyurethanes, Vol III, 2ed., Wiley & Sons, London (1998)

[28] Ranjbar Z, Montazeri S, Mohammad M, Nayini R, Jannesari A, Prog. Org. Coat., 69, 426 (2010)

[29] Seymour RW, Cooper SL, Macromolecules., 6, 48 (1973)

[30] Gedan-Smolka M, Haussler L, Fischer D, Thermochim. Acta, 351(1-2), 95 (2000)

[31] Woods G, The ICI Polyurethane Book, 2nd ed., Wiley & Sons, New York (1990)

[32] Nasar AS, Subramani S, Radhakrishnan G, Polym. Int., 48, 614 (1999)