Abstract
A series of novel random poly(benzoxazole-amide-imide) copolymers were synthesized via the poly(amic acid)s from the reaction of 5-amino-2-(4-aminophenyl)benzoxazole (BOA) and 4-amino-N-(4-aminophenyl)benzamide (DABA) with 3,3′,4,4′-biphenyltetracarboxylic dianhydride (BPDA). The corresponding homopolyimides were also prepared for comparison. The chemical composition, interchain hydrogen bonding and molecular arrangement of the copolyimides in solid films were investigated by attenuated total reflectance Fourier transform infrared (ATR-FTIR) spectroscopy, computation techniques and wide angle X-ray diffraction (WAXD). The results indicated that the interchain hydrogen bonds were most likely formed between the amide oxygen atoms and -N-H bands. And the ordered chain packing structures of copolyimide films were completely different from those of the homopolyimide films probably due to the directional interchain hydrogen bonding interactions. The properties of the copolyimides were also well-characterized by tensile tests, dynamic mechanical analysis (DMA), thermal gravimetric analysis (TGA) along with water absorption, solubility and peel tests. All of the obtained copolyimide films exhibited high tensile strength (321 ~ 332 MPa) and modulus (6.76 ~ 8.03 GPa) without any stretching. Moreover, the glass transition temperatures (T gs) and 5 % weight-loss temperatures of the copolyimides in nitrogen were above 322 and 560 °C, respectively. Additionally, the copolyimide films also exhibited low water absorption, excellent chemical resistance and good adhesion properties suitable for interlevel dielectrics in microelectronics.
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References
Tao LM, Yang HX, Liu JG, Fan L, Yang SY (2009) Polymer 50:6009–6018
Yang CP, Chen YC, Hsiao SH, Guo W, Wang HM (2010) J Polym Res 17:779–788
Liu CL, Kurosawa T, Yu AD, Higashihara T, Ueda M, Chen WC (2011) J Phys Chem C 115:5930–5939
Dixit BC, Dixit RB, Desai DJ (2010) J Polym Res 17:481–488
Hsiao SH, Wang HM, Chen WJ, Lee TM, Leu CM (2011) J Polym Sci Pol Chem 49:3109–3120
Kung YC, Hsiao SH (2011) J Mater Chem 21:1746–1754
Koohmareh G, Mohammadifard N (2011) J Polym Res 18:983–991
Liaw DJ, Wang KL, Huang YC, Lee KR, Lai JY, Ha CS (2012) Prog Polym Sci 37:907–974
Chung IS, Park CE, Ree M, Kim SY (2001) Chem Mater 13:2801–2806
Chen HL, Ho SH, Wang TH, Chen KM, Pan JP, Liang SM, Hung A (1994) J Appl Polym Sci 51:1647–1652
Kuorosawa T, Chueh CC, Liu CL, Higashihara T, Ueda M, Chen WC (2010) Macromolecules 43:1236–1244
You NH, Chueh CC, Liu CL, Ueda M, Chen WC (2009) Macromolecules 42:4456–4463
Qiu W, Chen CC, Xu L, Cui L, Paul DR, Koros WJ (2011) Macromolecules 44:6046–6056
Kratochvil AM, Koros WJ (2010) Macromolecules 43:4679–4687
Park CH, Lee CH, Sohn JY, Park HB, Guiver MD, Lee YM (2010) J Phys Chem B 114:12036–12045
Xiao Y, Dai Y, Chung TS, Guiver MD (2005) Macromolecules 38:10042–10049
Qiu WL, Chen CC, Kincer MR, Koros WJ (2011) Polymer 52:4073–4082
Seo J, Kang J, Cho K, Park CE (2002) J Adhes Sci Technol 16:1839–1851
Myung BY, Ahn CJ, Yoon TH (2005) J Appl Polym Sci 96:1801–1809
Ku CK, Ho CH, Lee YD (2005) J Adhes Sci Technol 19:909–925
Chan Park MB, Tan SS (2002) Int J Adhes Adhes 22:471–475
Thiruvasagam P, Vijayan M (2012) J Polym Res 19:9845
Hsu SL-C, Luo GW, Chen HT, Chuang SW (2005) J Polym Sci Part A Polym Chem 43:6020–6027
Wang HH, Wu SP (2003) J Appl Polym Sci 90:1435–1444
Wang S, Zhou HW, Dang GD, Chen CH (2009) J Polym Sci Part A: Polym Chem 47:2024–2031
Jia X, Chao D, Liu H, He L, Zheng T, Bian X, Wang C (2011) Polym Chem 2:1300–1306
Musto P, Karasz FE, MacKnight WJ (1989) Polymer 30:1012–1021
Liu XY, Gao GQ, Dong L, Ye GD, Gu Y (2009) Polym Adv Technol 20:362–366
Wang S, Bao G, Lu Z, Wu P, Han Z (2000) J Mater Sci 35:5873–5877
Garcia JM, Garcia FC, Serna F, de la Pena JL (2010) Prog Polym Sci 35:623–686
Luo L, Pang Y, Jiang X, Wang X, Zhang P, Chen Y, Peng C, Liu X (2011) J Polym Res 19:9783
Wu SY, Yuen SM, Ma CCM, Huang YL (2009) J Appl Polym Sci 113:2301–2312
Zhuang YB, Liu XY, Gu Y (2012) Polym Chem 3:1517–1525
Jou JH, Huang PT (1991) Macromolecules 24:3796–3803
Raharintsalama R, Munakata H, Koyama M, Kubo M, Miyamoto A (2005) Appl Surf Sci 244:631–635
Zhuang YB, Gu Y (2012) J Polym Res 19:14
Zhuang YB, Gu Y (2012) J Macromol Sci Part B: Phys 51:2157–2170
Anto PL, Panicker CY, Varghese HT, Philip D, Temiz-Arpaci O, Tekiner-Gulbas B, Yildiz I (2007) Spectrochim Acta Part A 67:744–749
Mary YS, Varghese HT, Panicker CY, Ertan T, Yildiz I, Temiz-Arpaci O (2008) Spectrochim Acta Part A 71:566–571
Ree M, Kim K, Woo SH, Chang H (1997) J Appl Phys 81:698–708
Ishii J, Takata A, Oami Y, Yokota R, Vladimirov L, Hasegawa M (2010) Eur Polym J 46:681–693
Ishii J, Shimizu N, Ishihara N, Ikeda Y, Sensui N, Matano T, Hasegawa M (2010) Eur Polym J 46:69–80
Lee KW, Viehbeck A, Walker GF, Cohen S, Zucco P, Chen R, Ree M (1996) J Adhes Sci Technol 10:807–821
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The work was supported by the National Natural Science Foundation of China (Grant NO. 50433010) and Construct Program of the Key Discipline in Hunan province (Applied Chemistry).
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Zhuang, Y., Gu, Y. Poly(benzoxazole-amide-imide) copolymers for interlevel dielectrics: interchain hydrogen bonding, molecular arrangement and properties. J Polym Res 20, 168 (2013). https://doi.org/10.1007/s10965-013-0168-7
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DOI: https://doi.org/10.1007/s10965-013-0168-7