Abstract
Two kinds of aromatic dibenzoyl chloride monomer containing thioether unit 4,4′-Bis(4-chloroformylphenylthio)benzophenone (BP-DC) and 4,4′-thiodibenzoyl chloride (T-DC) were synthesized with two steps, which was reacted with diamine monomer containing thioether and amide unit to prepare a new kind of polyamide containing high quantity thio-ether group. The intrinsic viscosity of the polyamides was 0.76–0.90 dl/g obtained with optimum synthesis conditions. The polymers were found to have good optical properties: the optical transmittance of the aromatic polyamide film at 450 nm is higher than 80%, meantime the high quantity thio-ether unit provided the polymer with a high refractive index ranging from 1.691 to 1.696 and low birefringence of 0.007–0.008. At the same time the polymers had excellent thermal performance with glass transition temperature (Tg) of 226 °C–278 °C, initial degradation temperature (Td) of 427 °C–439 °C. They showed improved solubility in polar aprotic solvents.
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Suwa M, Niwa H, Tomikawa M (2006) J Photopolym Sci Technol 19:275–276
Kunugi Y, Miller L, Maki T, Canavesi A (1997) Chem Mater 9:1061–1062
Geiger F, Stoldt M, Schweizer H, Bauerle P, Umbach E (1993) Adv Mater 5:922–925
Ju YG, Almuneau G, Kim TH, Lee BW (2006) Jpn J Appl Phys 45:2546–2549
Kitamura K, Okada K, Fujita N, Nagasaka Y, Ueda M, Sekimoto Y, Kurata Y (2004) Jpn J Appl Phys 43:5840–5844
Matsuda T, Funae Y, Yoshida M, Yamamoto T, Takaya T (2000) J Appl Polym Sci 76:45–49
Liu JG, Nakamura Y, Ogura T, Shibasaki Y, Ando S, Ueda M (2008) Chem Mater 20:273–281
Liu JG, Nakamura Y, Shibasaki Y, Ando S, Ueda M (2007) J Polym Sci Part A: Polym Chem 45:5606–5617
You NH, Nakamura Y, Suzuki Y, Higashihara T, Ando S, Ueda M (2009) J Polym Sci Part A: Polym Chem 47:4886–4894
You NH, Fukuzaki N, Suzuki Y, Nakamura Y, Higashihara T, Ando S, Ueda M (2009) J Polym Sci Part A: Polym Chem 47:4428–4434
Ando S, Fujigaya T, Ueda M (2002) J Appl Phys 41:L105–L108
Matsuda T, Funae Y, Yoshida M, Takaya T (1999) J Macromol Sci, Part A Pure Appl Chem A36:1271–1288
Sawada T, Ando S (1998) Chem Mater 10:3368–3378
Lu CL, Cui ZC, Wang YX, Yang B, Shen JC (2003) J Appl Polym Sci 89:2426–2430
Nebioglu A, Leon JA, Khudyakov IV (2008) Ind Eng Chem Res 47:2155–2159
Terraza CA, Liu JG, Nakamura Y, Shibasaki Y, Ando S (2008) J Polym Sci Part A: Polym Chem 346:1510–1520
Seesukphronrarak S, Kawasaki S, Kobori K, Takata T (2007) J Polym Sci Part A: Polym Chem 45:3073–3082
Liou GS, Lin PH, Yen HJ, Yu YY, Chen WC (2010) J Polym Sci Part A: Polym Chem 48:1433–1440
Yang J, Zhang G, Long SR, Wang XJ, Liu J, Chen YR (2008) CN Patent 101215379
Zhang G, Liu J, Zhang ML, Liu SL, Long SR, Yang J (2009) J Macromol Sci Part A: Pure and Appl Chem 46:1015–1023
Lucas M, Brock P, Hedrick JL (1993) J Polym Sci Part A: Polym Chem 31(9):2179–2185
Zhang G, Zhao TP, Wang YL, Liu SL, Long SR, Yang J (2010) J Macromol Sci Part A: Pure and Appl Chem 47:291–301
Yang J, Zhang G, Long SR, Wang XJ (2009) CN Patent 101429279
Liu JG, Nakamura Y, Shibasaki Y, Ando S, Ueda M (2007) Polym J 39:543–550
Williams FJ (1976) US Patent 3933862
Yan JL, Wang Z, Gao LX, Ding MX (2005) Polymer 46:7678–7683
Ding Y, Hay AS (1996) Macromolecules 29:6386–6392
Oishi Y, Kakimoto MA, Imai Y (1988) Macromolecules 21(3):547–550
Oishi Y, Kakimoto MA, Imai Y (1991) J Polym Sci Part A: Polym Chem 29(13):1925–1931
Mehdipour-Ataei S, Barikani M (1999) Iran Polym J 8(1):3–8
Mehdipour-Ataei S, Tadjarodi A, Babanzadeh S (2007) Eur Polym J 43(2):498–506
Liu JG, Nakamura Y, Shibasaki Y, Ando S, Ueda M (2007) Macromolecules 40:4614–4620
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This work was supported by research grants from National High Technology Foundation of China (863 program, Grant No.: 2007AA03Z561).
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Zhang, G., Huang, Gs., Wang, Xj. et al. Synthesis of high refractive index polyamides containing thioether unit. J Polym Res 18, 1261–1268 (2011). https://doi.org/10.1007/s10965-010-9528-8
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DOI: https://doi.org/10.1007/s10965-010-9528-8