식물성 오일 기반 Poly(β-amino ester) 합성

장나리; 김범수; Na-Ri Jang; Beom Soo Kim

Korean Chemical Engineering Research, Vol.50, No.6, 1064-1067, December, 2012

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식물성 오일 기반 Poly(β-amino ester) 합성

Synthesis of Vegetable Oil-Based Poly(β-amino ester)

장나리, 김범수 ^†

충북대학교 화학공학과, 361-763 충북 청주시 흥덕구 내수동로 52

Na-Ri Jang, and Beom Soo Kim^†

Department of Chemical Engineering, College of Engineering, Chungbuk National University, 52 Naesudong-ro, Heungduk-gu, Cheongju, Chungbuk 361-763, Korea

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초록

최근 저가의 풍부한 재생 가능 천연자원인 식물성 오일에 대한 관심이 증가되고 있다. 식물성 오일은 친환경적인 생분해성 고분자 물질들의 원료로서 사용될 수 있다. 본 연구에서는 acrylated epoxidized soybean oil (AESO)과 2-aminoethanol의 중합 반응에 의해 poly(β-amino ester)를 합성하였다. AESO와 2-aminoethanol의 몰비를 변화시켜 다양한 비율의 고분자 필름을 제조하였다. FT-IR을 이용하여 poly(β-amino ester) 내의 C-N 결합의 생성을 확인하였으며, 98% 이상의 겔함량으로부터 가교 고분자 네트웍이 합성되었음을 확인하였다. 고분자 필름의 인장강도와 신장률은 각각 0.3~1.3 MPa, 32~55%였다. 고분자 필름은 lipase 효소가 첨가된 pH 7.2 완충용액에서 35일 경과 후 2~7%의 질량 감소를 보였다.

Recently, there is a growing interest in vegetable oils, cheap and abundant renewable natural resources. Vegetable oils can be used as raw materials for ecofriendly biodegradable polymer materials. In this study, poly(β-amino esters) were synthesized by polymerization reaction of acrylated epoxidized soybean oil (AESO) and 2-aminoethanol. Various polymer films were prepared by changing the molar ratio of AESO to 2-aminoethanol. The formation of C-N bonds in poly(β-amino ester) was confirmed using FT-IR. Gel contents higher than 98% confirmed the synthesis of crosslinked polymer networks. Tensile strengths and elongation at breaks of polymer films ranged from 0.3 to 1.3 MPa and 32 to 55%, respectively. Polymer films degraded 2 to 7% of the initial weight in 35 days in phosphate buffer solution (pH 7.2) containing lipase enzyme.

Keywords:Poly(β-amino ester);Vegetable Oil;Acrylated Epoxidized Soybean Oil;2-aminoethanol

[References]

Shogren RL, Petrovic Z, Liu Z, Erhan SZ, J.Polym. Environ., 12, 173 (2004)
Sung IK, Song JY, Kim BS, Korean Chem. Eng. Res., 49(4), 475 (2011)
Kang KS, Lee SI, Lee TJ, Narayan R, Shin BY, Korean J. Chem. Eng., 25(3), 599 (2008)
Hou CT, in: Hou CT (Ed.) Handbook of Industrial Biocatalysis, CRC Press, 7-1~7-25 (2005)
Bonnaillie LM, Wool RP, J. Appl. Polym. Sci., 105(3), 1042 (2007)
Lu J, Khot S, Wool RP, Polymer., 46, 71 (2004)
Lu J, Hong CK, Wool RP, J. Polym. Sci. B: Polym. Phys., 42(8), 1441 (2004)
Rong MZ, Zhang MQ, Wu SP, Wang HJ, Czigany T, Mat. Sci. Forum., 539-543, 2311 (2007)
Lynn DM, Langer R, J. Am. Chem. Soc., 122(44), 10761 (2000)
Green JJ, Zugates GT, Langer R, Anderson DG, Methods Mol. Biol., 480, 53 (2009)
Kim HM, Kim HR, Kim BS, J. Polym. Environ., 18, 291 (2010)
Kim HM, Kim HR. Hou CT, Kim BS, J. Am. Oil Chem. Soc., 87, 1451 (2010)
Wu S, Rong M, Zhang M, Hu J, Acta Polym. Sin., 10, 993 (2007)

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[1] Shogren RL, Petrovic Z, Liu Z, Erhan SZ, J.Polym. Environ., 12, 173 (2004)

[2] Sung IK, Song JY, Kim BS, Korean Chem. Eng. Res., 49(4), 475 (2011)

[3] Kang KS, Lee SI, Lee TJ, Narayan R, Shin BY, Korean J. Chem. Eng., 25(3), 599 (2008)

[4] Hou CT, in: Hou CT (Ed.) Handbook of Industrial Biocatalysis, CRC Press, 7-1~7-25 (2005)

[5] Bonnaillie LM, Wool RP, J. Appl. Polym. Sci., 105(3), 1042 (2007)

[6] Lu J, Khot S, Wool RP, Polymer., 46, 71 (2004)

[7] Lu J, Hong CK, Wool RP, J. Polym. Sci. B: Polym. Phys., 42(8), 1441 (2004)

[8] Rong MZ, Zhang MQ, Wu SP, Wang HJ, Czigany T, Mat. Sci. Forum., 539-543, 2311 (2007)

[9] Lynn DM, Langer R, J. Am. Chem. Soc., 122(44), 10761 (2000)

[10] Green JJ, Zugates GT, Langer R, Anderson DG, Methods Mol. Biol., 480, 53 (2009)

[11] Kim HM, Kim HR, Kim BS, J. Polym. Environ., 18, 291 (2010)

[12] Kim HM, Kim HR. Hou CT, Kim BS, J. Am. Oil Chem. Soc., 87, 1451 (2010)

[13] Wu S, Rong M, Zhang M, Hu J, Acta Polym. Sin., 10, 993 (2007)