Castor 오일과 HER 기반 폴리우레탄: 합성, 분석, 구조-열 안정성 상관관계

Thangamani Rajkumar; Venugopalan Rajasudha; Arunjunai Raj Mahendran; Chinnaswamy Thangavel Vijayakumar

Polymer(Korea), Vol.45, No.4, 511-519, July, 2021

DOI10.7317/pk.2021.45.4.511 Export Citation

Castor 오일과 HER 기반 폴리우레탄: 합성, 분석, 구조-열 안정성 상관관계

Castor Oil and HER Based Polyurethanes: Synthesis, Characterization and Structure-Thermal Stability Relation

Thangamani Rajkumar^†, Venugopalan Rajasudha¹, Arunjunai Raj Mahendran², and Chinnaswamy Thangavel Vijayakumar³

Department of Chemistry, Rajah Serfoji Government College (Affiliated to Bharathidasan University), Thanjavur - 613005, Tamilnadu, India
¹Department of Chemistry, Bon Secours College for Women, Thanjavur - 613006, Tamilnadu, India
²Wood K Plus-Competence Center for Wood Composites and Wood Chemistry, Altenberger Strasse 69, A-4040 Linz, Austria
³Department of Polymer Technology, Kamaraj College of Engg. & Tech., S.P.G.C. Nagar, K. Vellakulam Post - 625701, Tamilnadu, India

E-mail:

Polyurethanes (PUs) were prepared from solvent and catalyst free reaction mixture containing polyethylene glycol (PEG), 4,4’-methylene diphenyl diisocyanate (MDI) and 1,3-bis(2-hydroxyethoxy) benzene (HER) and/or castor oil (CAO). PUs were characterized using the Fourier-transform infrared spectroscopy (FTIR) and proton nuclear magnetic resonance (1H NMR) spectroscopic methods. Thermal studies on PUs using differential scanning calorimetric (DSC) and thermogravimetric analysis coupled with FTIR (TG/FTIR) proved that CAO-extended PUs were thermally more stable than HER extended PUs. The partial and complete replacement of HER content in PUs using CAO enhanced the thermal stability by shifting degradation temperature to higher temperature (5-15 °C) and enhancing the char residue. The parameters derived from DSC traces, thermogram and differential thermogram confirmed that PUs synthesized using PEG 1500 are thermally more stable than the PUs prepared using PEG 4000. The probable degradation mechanism to study the role of β-hydrogen on the thermal stability was proposed and discussed based on the results of TG/FTIR.

Keywords:β-hydrogen;mechanism;polyurethane;synthesis;thermal degradation

[References]

Handbook of Elastomers: New Developments and Technology, Marcel Decker: New York, USA, 1988.
Wirpsza Z, Polyurethane Chemistry, Technology and Applications; York, USA, 1993.
Wu S, Bulpett DA, Harris KM, Lutz ME, Rajagopalan M, US Patent 6,435,986, 2002.
Durairaj PB, Resorcinol: Chemistry, Technology and Applications 2005.
Opera S, High Perform. Polym., 24, 389 (2012)
Wang HH, Yuen UE, J. Appl. Polym. Sci., 102(1), 607 (2006)
Mattia J, Painter PAA, Macromol, 40, 1546 (2007)
Rogulska M, Kultys A, Podkoscielny W, Eur. Polym. J., 43, 1402 (2007)
Kausar A, Zulfiqar S, Ahmad Z, Sarwar MI, Polym. Degrad. Stabil., 95, 2281 (2010)
Kultys A, Rogulska M, Gluchowska H, Polym. Int., 60, 652 (2011)
Wu S, Polyurethane Golf Ball with Improved Resiliency. US Patent 6,210,294 B1, 2002.
Delebecq E, Pascault JP, Boutevin B, Ganachaud F, Chem. Rev., 113(1), 80 (2013)
Helou M, Carpentier JF, Guillaume SM, Green Chem., 13, 266 (2011)
Javni I, Hong DP, Petrovic ZS, J. Appl. Polym. Sci., 128(1), 566 (2013)
Diakoumakos CD, Kotzev DL, Macromol. Symp., 216, 37 (2004)
Orgiles-Calpena E, Aran-Ais A, Torro-Palau AM, Orgiles-Barcelo C, Proc. Inst. Mech. Eng. L, 228, 125 (2014)
Desroches M, Escouvois M, Auvergne R, Caillol S, Boutevin B, Polym. Rev., 52, 38 (2012)
Lligadas G, Ronda JC, Galia M, Cadiz V, Biomacromolecules, 11(11), 2825 (2010)
Howard GT, Int. Biodeter. Biodegrad., 49, 245 (2002)
Gonzaga, Gonzaga DP, Murakami CR, Chierice GO, Altafim RAC, Electrical Characterization of Castor-oil Resins, Arlington, VA, June 7-10, p.181, 1998.
Das S, Pandey P, Mohanty S, Nayak S, Polym. Plast. Technol. Eng., 56, 1556 (2017)
Tran TK, Kumar P, Kim HR, Hou CT, Kim BS, J. Am. Oil Chem. Soc., 96, 715 (2019)
Zhang J, Yao M, Chen J, Jiang Z, Ma Y, J. Appl. Polym. Sci., 136, 47309 (2019)
Arevalo-Alquichire S, Valero M, Elastomers, pp.137, 2017.
Levesque S, Rodrigue D, Vermette P, Gunatillake P, Biomedical Applications of Polyurethanes, pp.22, 2001.
Huang KS, Chen SW, Lu LA, Min RR, Cellul. Chem. Technol., 41, 113 (2007)
Li XX, Jin KH, Cho UR, Polym. Korea, 43(4), 595 (2019)
Li XX, Sohn MH, Cho UR, Polym. Korea, 43(4), 621 (2019)
Chen Z, Nikos H, Feng X, Gnanou Y, Macromol., 50, 2320 (2017)
Conceicao MM, Fernandes VJ, Araujo AS, Farias MF, Santos IMG, Souza AG, Energy Fuels, 21(3), 1522 (2007)
Wong C, Badri K, Mater. Sci. Appl., 3, 78 (2011)
Saunders JH, Rubber Chem. Technol., 32, 337 (1959)
Saunders JH, Backus JK, Rubber Chem. Technol., 39, 461 (1966)
Vijayakumar CT, Sivasamy P, Rajkumar T, Eur. Polym. J., 43, 3028 (2007)
Sivasamy P, Palaniandavar M, Vijayakumar CT, Lederer K, Polym. Degrad. Stabil., 38, 15 (1992)
Backus JK, Darr WC, Gemeinhardt PG, Saunders JH, J. Cell. Plast., 1, 178 (1965)
Mead MJ, Mechanical Degradation of a Polyurethane Elastomer, USA, 1986.
Pabbo M, Levin BC, Fire Mater., 11, 1 (1987)

[1] Handbook of Elastomers: New Developments and Technology, Marcel Decker: New York, USA, 1988.

[2] Wirpsza Z, Polyurethane Chemistry, Technology and Applications; York, USA, 1993.

[3] Wu S, Bulpett DA, Harris KM, Lutz ME, Rajagopalan M, US Patent 6,435,986, 2002.

[4] Durairaj PB, Resorcinol: Chemistry, Technology and Applications 2005.

[5] Opera S, High Perform. Polym., 24, 389 (2012)

[6] Wang HH, Yuen UE, J. Appl. Polym. Sci., 102(1), 607 (2006)

[7] Mattia J, Painter PAA, Macromol, 40, 1546 (2007)

[8] Rogulska M, Kultys A, Podkoscielny W, Eur. Polym. J., 43, 1402 (2007)

[9] Kausar A, Zulfiqar S, Ahmad Z, Sarwar MI, Polym. Degrad. Stabil., 95, 2281 (2010)

[10] Kultys A, Rogulska M, Gluchowska H, Polym. Int., 60, 652 (2011)

[11] Wu S, Polyurethane Golf Ball with Improved Resiliency. US Patent 6,210,294 B1, 2002.

[12] Delebecq E, Pascault JP, Boutevin B, Ganachaud F, Chem. Rev., 113(1), 80 (2013)

[13] Helou M, Carpentier JF, Guillaume SM, Green Chem., 13, 266 (2011)

[14] Javni I, Hong DP, Petrovic ZS, J. Appl. Polym. Sci., 128(1), 566 (2013)

[15] Diakoumakos CD, Kotzev DL, Macromol. Symp., 216, 37 (2004)

[16] Orgiles-Calpena E, Aran-Ais A, Torro-Palau AM, Orgiles-Barcelo C, Proc. Inst. Mech. Eng. L, 228, 125 (2014)

[17] Desroches M, Escouvois M, Auvergne R, Caillol S, Boutevin B, Polym. Rev., 52, 38 (2012)

[18] Lligadas G, Ronda JC, Galia M, Cadiz V, Biomacromolecules, 11(11), 2825 (2010)

[19] Howard GT, Int. Biodeter. Biodegrad., 49, 245 (2002)

[20] Gonzaga, Gonzaga DP, Murakami CR, Chierice GO, Altafim RAC, Electrical Characterization of Castor-oil Resins, Arlington, VA, June 7-10, p.181, 1998.

[21] Das S, Pandey P, Mohanty S, Nayak S, Polym. Plast. Technol. Eng., 56, 1556 (2017)

[22] Tran TK, Kumar P, Kim HR, Hou CT, Kim BS, J. Am. Oil Chem. Soc., 96, 715 (2019)

[23] Zhang J, Yao M, Chen J, Jiang Z, Ma Y, J. Appl. Polym. Sci., 136, 47309 (2019)

[24] Arevalo-Alquichire S, Valero M, Elastomers, pp.137, 2017.

[25] Levesque S, Rodrigue D, Vermette P, Gunatillake P, Biomedical Applications of Polyurethanes, pp.22, 2001.

[26] Huang KS, Chen SW, Lu LA, Min RR, Cellul. Chem. Technol., 41, 113 (2007)

[27] Li XX, Jin KH, Cho UR, Polym. Korea, 43(4), 595 (2019)

[28] Li XX, Sohn MH, Cho UR, Polym. Korea, 43(4), 621 (2019)

[29] Chen Z, Nikos H, Feng X, Gnanou Y, Macromol., 50, 2320 (2017)

[30] Conceicao MM, Fernandes VJ, Araujo AS, Farias MF, Santos IMG, Souza AG, Energy Fuels, 21(3), 1522 (2007)

[31] Wong C, Badri K, Mater. Sci. Appl., 3, 78 (2011)

[32] Saunders JH, Rubber Chem. Technol., 32, 337 (1959)

[33] Saunders JH, Backus JK, Rubber Chem. Technol., 39, 461 (1966)

[34] Vijayakumar CT, Sivasamy P, Rajkumar T, Eur. Polym. J., 43, 3028 (2007)

[35] Sivasamy P, Palaniandavar M, Vijayakumar CT, Lederer K, Polym. Degrad. Stabil., 38, 15 (1992)

[36] Backus JK, Darr WC, Gemeinhardt PG, Saunders JH, J. Cell. Plast., 1, 178 (1965)

[37] Mead MJ, Mechanical Degradation of a Polyurethane Elastomer, USA, 1986.

[38] Pabbo M, Levin BC, Fire Mater., 11, 1 (1987)