두 단계의 반응을 통해 개질된 카다놀 유래 바이오폴리올 기반의 폴리우레탄 필름의 합성 및 특성 분석

김성현; 김성우; 차상호; Sung-Hyun Kim; Seong Woo Kim; Sang-Ho Cha

Polymer(Korea), Vol.40, No.6, 1005-1014, November, 2016

DOI10.7317/pk.2016.40.6.1005 Export Citation

두 단계의 반응을 통해 개질된 카다놀 유래 바이오폴리올 기반의 폴리우레탄 필름의 합성 및 특성 분석

Synthesis and Characterization of Biopolyol-based Polyurethane Films Derived from Modified Cardanol through Two-step Reaction

김성현, 김성우, 차상호^†

경기대학교 화학공학과

Sung-Hyun Kim, Seong Woo Kim, and Sang-Ho Cha^†

Department of Chemical Engineering, Kyonggi University, Iui-dong, Yeongtong-gu, Suwon-si, Gyeonggi-do 16227, Korea

E-mail:

초록

본 연구에서는 식물유 중 하나인 카다놀로부터 합성된 바이오 기반의 폴리올을 이용하여 폴리우레탄 필름을 제조하였다. 카다놀 기반의 바이오 폴리올은 포름산과 과산화수소를 통한 에폭시화 반응 후 각각 다른 치환체들에 의한 개환반응을 이용하여 제조하였다. 바이오 폴리올의 분자 구조는 FTIR과 NMR(1H and 13C)을 통하여 분석하였으며, 추가적으로 GPC를 이용하여 올리고머화를 확인하였다. 폴리우레탄 필름은 합성 바이오 폴리올과 hexamethylene diisocyanate(HDI), 촉매인 DBTDL을 사용하여 제조하였으며, 필름의 기계적 및 열적 물성은 DSC, TGA, 접촉각 측정, 그리고 UTM을 이용하여 분석하였다. 분석 결과, Polyol(TEG)를 사용한 PU 필름이 다른 PU 필름에 비해 높은 인장강도와 열적 안정성을 갖는 것으로 나타났다.

In this study, a bio-based polyol was prepared from cardanol, one of the vegetable oil. The cardanol-based biopolyol was synthesized using chemical modification of the cardanol by epoxidation reaction with formic acid (HCOOH) and hydrogen peroxide (H2O2), followed by ring-opening reaction with different reaction reagents. The molecular structure of cardanol-based biopolyol was characterized FTIR and NMR (1H and 13C). Additionally, we confirmed their oligomerization by GPC. Polyurethane (PU) films were manufactured from cardanol - based biopolyol and hexamethylene diisocyanate (HDI) with dibutyltin dilaurate (DBTDL) as a catalyst. The mechanical and thermal properties of PUs were characterized by DSC, TGA, contact angle measurement and UTM. The experimental results revealed that PU film derived from Polyol (TEG) exhibits higher tensile strength and thermal stability than other PU flims.

Keywords:cardanol;biopolyol;polyurethane;mechanical property;thermal stability

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[Referenced By]

[1] Randall D, Lee S, The polyurethanes book, John Wiley & Sons. lnc., Hoboken, NJ, 2002.

[2] Pfister DP, Xia Y, Larock RC, Chem. Sus. Chem., 4, 703 (2011)

[3] No SY, Renew. Sust. Energ. Rev., 15, 131 (2011)

[4] Petrovi ZS, Polym. Rev., 48, 109 (2008)

[5] Xia Y, Larock RC, Green Chem., 12, 1893 (2010)

[6] Miao S, Wang P, Su Z, Zhang S, Acta Biomater., 10, 1692 (2014)

[7] Alagi P, Hong SC, Macromol. Res., 23(12), 1079 (2015)

[8] da Silva EAB, Zabkova M, Araujo JD, Cateto CA, Barreiro MF, Belgacem MN, Rodriques AE, Chem. Eng. Res. Des., 87(9A), 1276 (2009)

[9] Yao YG, Yoshioka M, Shiraishi N, J. Appl. Polym. Sci., 60(11), 1939 (1996)

[10] Yan YB, Pang H, Yang XX, Zhang RL, Liao B, J. Appl. Polym. Sci., 110(2), 1099 (2008)

[11] Petrovic ZS, Wan X, Bilic O, Zlatanic A, Hong J, Javni I, Ionescu M, Milic J, Degruson D, J. Am. Oil Chem. Soc., 90, 1073 (2013)

[12] Yeganeh H, Mehdizadeh MR, Eur. Polym. J., 40, 1233 (2004)

[13] Choi KK, Park SH, Oh KW, Kim SH, Macromol. Res., 23(4), 333 (2015)

[14] Milchert E, Smagowicz A, Lewandowski G, Org. Process Res. Dev., 14, 1094 (2010)

[15] Meshram PD, Puri RG, Patil AL, Gite VV, J. Coat. Technol. Res., 10, 331 (2010)

[16] Pawlik H, Prociak A, J. Polym. Environ., 20, 438 (2012)

[17] Hazmi ASA, Aung MM, Abdullah LC, Salleh MZ, Mahmood MH, Ind. Crop. Prod., 50, 563 (2013)

[18] de Souza VHR, Silva SA, Ramos LP, Zawadzki SF, J. Am. Oil Chem. Soc., 89, 1723 (2012)

[19] Tran P, Graiver D, Narayan R, J. Am. Oil Chem. Soc., 82, 653 (2005)

[20] Cvetkovic I, Milic J, Ionescu M, Petrovi ZS, Hem. Ind., 62, 319 (2008)

[21] Guo A, Demydov D, Zhang W, Petrovic ZS, J. Polym. Environ., 10, 49 (2002)

[22] Dai H, Yang L, Lin B, Wang C, Shi G, J. Am. Oil Chem. Soc., 86, 261 (2009)

[23] Ji D, Fang Z, He W, Luo Z, Jiang X, Wang T, Guo K, Ind. Crop. Prod., 74, 76 (2015)

[24] Mosiewicki MA, Rojek P, Michałowski S, Aranguren MI, Prociak A, J. Appl. Polym. Sci., 132 (2015)

[25] Zhang C, Madbouly SA, Kessler MR, ACS Appl. Mater. Interfaces, 7, 1226 (2015)

[26] Wang CS, Yang LT, Ni BL, Shi G, J. Appl. Polym. Sci., 114, 125 (2015)

[27] Kong X, Liu G, Curtis JM, Eur. Polym. J., 48, 2097 (2012)

[28] Liu J, Liu R, Zhang X, Li Z, Tang H, Liu X, Prog. Org. Coat., 90, 126 (2016)

[29] Rao B, Palanisamy A, Eur. Polym. J., 49, 2365 (2013)

[30] Kathalewar M, Sabnis A, D’Melo D, Prog. Org. Coat., 77, 616 (2014)

[31] Jaillet F, Darroman E, Ratsimihety A, Auvergne R, Boutevin B, Caillol S, Eur. J. Lipid Sci. Technol., 116, 63 (2014)

[32] Sultania M, Rai J, Srivastava D, Eur. Polym. J., 46, 2019 (2010)

[33] Suresh KI, Kishanprasad VS, Ind. Eng. Chem. Res., 44(13), 4504 (2005)