화학공학소재연구정보센터
Macromolecular Research, Vol.29, No.4, 257-266, April, 2021
Carbazole-Based Hyperbranched Polyester Polyol: Structural, Rheological, Thermal and Optical Properties
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The present study sought to obtain a hyperbranched polyester polyol derivative with fluorescent properties. Initially, a 4-((4-(9H-carbazol-9-yl)benzyl)oxy)- 4-oxobut-2-enoic acid (CAV) was synthesized and esterified with a hyperbranched polyester polyol obtained from fourth generation (HBP) to synthesize carbazolebased hyperbranched polyester polyols (HBPCAV). The proportions employed of CAV were 5, 10, 15, and 20 wt% relative to that of HBP. The grafted CAV percentage (P gCAV) increased with the CAV content. The conversion percentages (CP) of the reactions for obtaining HBPCAV were higher than 95% and the hydroxyl values (OHV) were lower than that of HBP. The modification percentage (MP) of the HBP was between 9.33 and 27.38%. Using proton nuclear magnetic resonance (1H NMR) and infrared (IR) analyses was evidenced the formation of CAV and HBPCAV. Dynamic light scattering (DLS) analysis showed that HBPCAV exhibited aggregations. The number average molar mass (M n), viscosity (η), and glass transition temperature (T g) values of the HBPCAV samples were higher than those of the HBP, and also increased with the P gCAV values. The rheological behaviors of the HBP and HBPCAV samples were mainly Newtonian and shear-thinning, respectively. All HBPCAV exhibited electroluminescent properties.
  1. Liu C, Wang D, Wang W, Song Y, Li Y, Zhou H, Chen C, Zhao X, Polym. J., 45, 318 (2013)
  2. Zagar E, Zigon M, Prog. Polym. Sci, 36, 53 (2011)
  3. Thomasson D, Boisson F, Girard-Reydet E, Mechin F, React. Funct. Polym., 66(12), 1462 (2006)
  4. Zagar E, Zigon M, Macromolecules, 35(27), 9913 (2002)
  5. Bat E, Gunduz G, Kisakurek D, Akhmedov IM, Prog. Org. Coat., 55, 330 (2006)
  6. Mesias R, Murillo EA, J. Appl. Polym. Sci., 132, 1 (2015)
  7. Gataulina AR, Khannanov AA, Malinovskikh OA, Bondar’ OV, Ulakhovich NA, Kutyreva MR, Russ. J. Gen. Chem., 83, 2269 (2013)
  8. Ikladious NE, Asaad JN, Rozik NN, Des. Monomers Polym., 12, 469 (2009)
  9. Vallejo PP, Lopez BL, Murillo EA, Prog. Org. Coat., 87, 213 (2015)
  10. Guzman M, Giraldo D, Murillo E, Polimeros, 27, 1 (2017)
  11. Zhang FF, Gan LL, Zhou CH, Bioorg. Med. Chem. Lett., 20, 1881 (2010)
  12. Grazulevicius JV, Strohriegl P, Pielichowski J, Pielichowski K, Prog. Polym. Sci, 28, 1297 (2003)
  13. Bashir M, Bano A, Ijaz AS, Chaudhary BA, Molecules, 20, 13496 (2015)
  14. Lee SB, Park SN, Kim C, Lee HW, Lee HW, Kim YK, Yoon SS, Synth. Met., 203, 174 (2015)
  15. Baronas P, Kazlauskas K, Kreiza G, Jankauskas V, Tomkeviciene A, Simokaitiene J, Grigalevicius S, Grazulevicius VJ, Jursenas S, Dyes Pigment., 123, 370 (2015)
  16. Ates M, Uludag N, Karazehir T, Arican F, Express Polym. Lett., 8, 480 (2014)
  17. Zhao C, Ouyang K, Yang N, Zhang J, Yang Z, Macromol. Res., 24(5), 393 (2016)
  18. Choi SS, Lee AS, Lee HS, Baek KY, Choi DH, Hwang SS, Macromol. Res., 19(3), 261 (2011)
  19. Cantillo R, Murillo EA, Percino J, J. Phys. Conf. Ser., 1386, 1 (2019)
  20. Yi X, Huang M, Qi Y, Gao E, Dalt. Trans., 43, 3691 (2014)
  21. He QY, Lai WY, Ma Z, Chen DY, Huang W, Eur. Polym. J., 44, 3169 (2008)
  22. Yang PC, Wu H, Wen HW, Hung WN, Eur. Polym. J., 49, 2303 (2013)
  23. Korychenska O, Acebo C, Bezuglyi M, Serra A, Grazulevicius JV, React. Funct. Polym., 106, 86 (2016)
  24. Qu JQ, Shiotsuki M, Kobayashi N, Sanda F, Masuda T, Polymer, 48(22), 6481 (2007)
  25. Li X, Zhao H, Gao L, Xie X, Zhang W, Wang M, Wu Y, Miao Y, Wang H, Xu B, RSC Adv., 9, 36058 (2019)
  26. Wu Y, Wu D, Zhao H, Li J, Li X, Wang Z, Wang H, Zhu F, Xu B, RSC Adv., 9, 22176 (2019)
  27. Cao PF, Rong LH, de Leon A, Su Z, Advincula RC, Macromolecules, 48(19), 6801 (2015)
  28. Wu W, Ye S, Huang L, Xiao L, Fu Y, Huang Q, Yu G, Liu Y, Qin J, Li Q, Li Z, J. Mater. Chem., 22, 6374 (2012)
  29. Lopez BL, Murillo EA, Vallejo PP, Sierra L, J. Appl. Polym. Sci., 116(5), 2658 (2010)
  30. Murillo EA, Vallejo PP, Lopez BL, E-Polymers, 10, 1347 (2010)
  31. Methods ST, Standard Test Methods for Testing Polyurethane Raw Materials: Determination of Hydroxyl Numbers of Polyols, Vol.08 2000.
  32. Ezeh IE, Umoren SA, Essien EE, Udoh AP, Ind. Crop. Prod., 36, 94 (2012)
  33. Xu P, Zhu X, Cong P, Du X, Zhang R, Constr. Build. Mater., 165, 295 (2018)
  34. Ararat CA, Quinonez W, Murillo EA, Macromol. Res., 27(7), 693 (2019)
  35. Zagar E, Zigon M, J. Chromatogr. A, 1034, 77 (2004)
  36. Jia M, Jiang L, Niu F, Zhang Y, Sun X, R. Soc. Open Sci., 5, 171988 (2019)
  37. Zhang M, Colby RH, Milner ST, Chung TCM, Huang TZ, deGroot W, Macromolecules, 46(11), 4313 (2013)
  38. Wang Q, Huang X, Nakamura A, Burchard W, Hallett FR, Carbohydr. Res., 340, 2637 (2005)
  39. Wong NA, Uchida NV, Dissanayake TU, Patel M, Iqbal M, Woehl TJ, J. Pharm. Sci., 109, 881 (2020)
  40. Chikh L, Tessier M, Fradet A, Polymer, 48(7), 1884 (2007)
  41. Vukovic J, Synthesis and Characterization of Aliphatic Hyperbranched Polyesters, Universitat Osnabruck, 2006.
  42. Xu M, Yan X, Cheng R, Yu X, Polym. Int., 50, 1338 (2001)
  43. Dumur F, Beouch L, Peralta D, Wantz G, Goubard F, Gigmes D, Org. Electron., 25, 21 (2015)
  44. Wei ZH, Xu JK, Nie GM, Du YK, Pu SZ, J. Electroanal. Chem., 589(1), 112 (2006)
  45. Zhang T, Xu DQ, Chen JM, Zhang P, Wang XC, Chinese Chem. Lett., 27, 441 (2016)
  46. Bu J, Duan H, Wang X, Xu T, Meng X, Qin D, Res. Chem. Intermed., 41, 2767 (2015)
  47. Liu J, Li W, Wang B, Tan M, He Y, Miao T, Lu X, Fu G, He H, Opt. Mater., 107, 1 (2020)
  48. Albrecht K, Matsuoka K, Fujita K, Yamamoto K, Angew. Chem.-Int. Edit., 54, 5677 (2015)
  49. Ricci RW, Nesta JM, J. Phys. Chem., 80, 974 (1976)
  50. Johnson GE, J. Phys. Chem., 84, 2940 (1980)
  51. Shi H, Xin D, Di Bai S, Fang L, Duan XE, Roose J, Peng H, Chen S, Tang BZ, Org. Electron., 33, 78 (2016)