화학공학소재연구정보센터
Journal of Industrial and Engineering Chemistry, Vol.92, 287-296, December, 2020
Solvent-free and anticounterfeiting fluorescent inks based on epoxy-functionalized polyacrylic nanoparticles modified with Rhodamine B for cellulosic substrates
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Nowadays, anticounterfeiting technology and information security by solvent-free photoluminescent polymeric latex nanoparticles are of considerable interest in variety of hi-tech systems. Herein and for the first time, Rhodamine B ethylenediamine acrylate (N-RhBAc) was synthesized and copolymerized with methyl methacrylate and glycidyl methacrylate to obtain epoxy-functionalized fluorescent latex nanoparticles (RhAcL-series) through emulsion polymerization. Inclusion of N-RhBAc into the spherical polyacrylic nanoparticles with average particle size of 40-70 nm enhanced its absorption intensity (λmax of 571 nm) and emission intensity (λem of 588 nm) up to 8 and 3.5-fold with respect to N-RhBAc in the solution state (λmax of 524 nm and λem of 582 nm), respectively. The nanometric size of particles and decorated epoxy functional groups on their outer layer provided well-wetting and fine-diffusion into the cellulosic nanofiber. To obtain anticounterfeiting inks with high-resolution marking on cellulosic paper without spreading and tracing, fluorescent RhAcL-1 was formulated with required thickening agent and defoamer. The painted pattern by the above ink could immediately be developed and illuminated with brilliant red-pink fluorescence emission upon UV irradiation.
  1. Cova L, Bigini P, Diana V, Sitia L, Ferrari R, Pesce RM, Khalaf R, Bossolasco P, et al., Nanotechnology, 24(24), 245603 (2013)
  2. Changizi O, Khoei S, Mahdavian A, Shirvalilou S, Mahdavi SR, Rad JK, Photodiagn. Photodyn. Ther., 29, 101602 (2020)
  3. Hu Y, Liang X, Zhuang Z, Cao Z, Qi Q, Wang Y, Mi Y, Zhao Z, Cui Q, Polym. Chem., 10(30), 4220 (2019)
  4. Cao Z, Liang X, Chen H, Gao M, Zhao Z, Chen X, Xu C, Qu G, Qi D, Tang BZ, Polym. Chem., 7(35), 5571 (2016)
  5. Rad JK, Ghomi AR, Karimipour K, Mandavian AR, Macromolecules, 53(5), 1613 (2020)
  6. Gui R, An X, Su H, Shen W, Zhu L, Ma X, Chen Z, Wang X, Talanta, 94, 295 (2012)
  7. Prakash K, Sahoo PR, Kumar S, Sens. Actuators B-Chem., 237, 856 (2016)
  8. Sahoo PR, Prakash K, Kumar S, Coord. Chem. Rev., 357, 18 (2018)
  9. Ciardelli F, Ruggeri G, Pucci A, Chem. Soc. Rev., 42(3), 857 (2013)
  10. Wang Q, Chen G, Yu Z, Ouyang X, Tian J, Yu M, ACS Sustain. Chem. Eng., 6(11), 13960 (2018)
  11. Yang Y, Zhang T, Yan JJ, Fu LW, Xiang HP, Cui YY, Su JH, Liu XX, Langmuir, 34(51), 15812 (2018)
  12. Sun M, Lv J, Xu H, zhang L, Zhong Y, Chen Z, Sui X, Wang B, Feng X, Mao Z, Cellulose, 27(5), 2939 (2020)
  13. Bao B, Fan J, Wang W, Yu D, Cellulose, 27(11), 6591 (2020)
  14. Kumar P, Singh S, Gupta BK, Nanoscale, 8(30), 14297 (2016)
  15. Park JH, Yoon SH, Heo NY, Lee WM, J. Ind. Eng. Chem., 88, 117 (2020)
  16. D’Halluin M, Rull-Barrull J, Le Grognec E, Jacquemin D, Felpin FX, Chem. Commun., 52, 7672 (2016)
  17. Irie M, Chem. Rev., 100(5), 1685 (2000)
  18. Zuo M, Qian W, Li T, Hu XY, Jiang J, Wang L, ACS Appl. Mater. Interfaces, 10(45), 39214 (2018)
  19. Evangelista AJ, Ivanchenko M, Myers AF, McAnulty LN, Payne GKM, Jing H, J. Mater. Chem. C, 8(17), 5692 (2020)
  20. Gao C, Zhang Z, Xing T, Hou X, Chen G, J. Mol. Liq., 297, 111783 (2020)
  21. Liang X, Tao M, Wu D, Yu B, Mi Y, Cao Z, Zhao Z, Chen D, Dyes Pigment., 177, 108287 (2020)
  22. You M, Zhong J, Hong Y, Duan Z, Lin M, Xu F, Nanoscale, 7(10), 4423 (2015)
  23. Ren W, Lin G, Clarke C, Zhou J, Jin D, Adv. Mater., 1901430 (2019).
  24. Shieh JY, Kuo JY, Weng HP, Yu HH, Langmuir, 29(2), 667 (2013)
  25. Liu J, Huang Y, Kumar A, Tan A, Jin S, Mozhi A, Liang XJ, Biotechnol. Adv., 32(4), 693 (2014)
  26. Liang X, Hu Y, Cao Z, Xiao L, Lou J, Liu L, Wang Y, Zhao Z, Qi D, Cui Q, Dyes Pigment., 163, 371 (2019)
  27. Rad JK, Alinejad Z, Khoei S, Mahdavian AR, ACS Biomater. Sci. Eng., 5(9), 4425 (2019)
  28. Hu Y, Liang X, Wu D, Yu B, Wang Y, Mi Y, Cao Z, Zhao Z, J. Mater. Chem. C, 8(2), 734 (2020)
  29. Rad JK, Mahdavian AR, Eur. Polym. J., 88, 56 (2017)
  30. Kwon JY, Jang YJ, Lee YJ, Kim KM, Seo MS, Nam W, Yoon J, J. Am. Chem. Soc., 127(28), 10107 (2005)
  31. Beija M, Afonso CAM, Martinho JMG, Chem. Soc. Rev., 38(8), 2410 (2009)
  32. Yan Y, Ding G, Xu H, J. Ind. Eng. Chem., 25, 73 (2015)
  33. Stephenson CJ, Shimizu KD, Org. Biomol. Chem., 8(5), 1027 (2010)
  34. Gao F, Wang L, Tang L, Zhu C, Microchim. Acta, 152(1-2), 131 (2005)
  35. Nghia NN, Huy BT, Lee YI, J. Ind. Eng. Chem., 81, 352 (2020)
  36. Zhu MQ, Zhang GF, Hu Z, Aldred MP, Li C, Gong WL, Chen T, Huang ZL, Liu SY, Macromolecules, 47(5), 1543 (2014)
  37. Zhu MQ, Zhang GF, Li C, Aldred MP, Chang E, Drezek RA, Li ADQ, J. Am. Chem. Soc., 133(2), 365 (2011)
  38. Valeur B, Berberan-Santos MN, Molecular fluorescence: principles and applications, 2nd ed., Wiley-VCH Verlag & Co, KGaA, Weinheim, Germany, 2012.
  39. Liang X, Hu Y, Lou J, Cao Z, Liu L, Wang Y, Zhao Z, Qi D, Cui Q, Dyes Pigment., 160, 572 (2019)
  40. Arık M, Celebi N, Onganer Y, J. Photochem. Photobiol. A-Chem., 170(2), 105 (2005)
  41. Rad JK, Mahdavian AR, Salehi-Mobarakeh H, Abdollahi A, Macromolecules, 49(1), 141 (206)
  42. Xuan J, Tian J, Cellulose, 25(7), 4067 (2018)
  43. Delavari S, Ziadzade S, Rad JK, Hamrang V, Mahdavian AR, Carbohydr. Polym., 247, 116756 (2020)
  44. Schafer CG, Gallei M, Zahn JT, Engelhardt J, Hellmann GP, Rehahn M, Chem. Mater., 25(11), 2309 (2013)
  45. Rull-Barrull J, D’Halluin M, Le Grognec E, Felpin FX, Chem. Commun., 52(12), 2525 (2016)
  46. Rull-Barrull J, D’Halluin M, Le Grognec E, Felpin FX, J. Mater. Chem. C, 5(21), 5154 (2017)
  47. Rad JK, Mahdavian AR, J. Phys. Chem. C, 120(18), 9985 (2016)
  48. Rad JK, Mahdavian AR, Iran. J. Polym. Sci. Technol., 30(5), 435 (2017)
  49. Bretel G, Le Grognec E, Jacquemin D, Hirose T, Matsuda K, Felpin FX, ACS Appl. Polym. Mater., 1(5), 1240 (2019)
  50. Karimipour K, Rad JK, Ghomi AR, Salehi-Mobarakeh H, Mahdavian AR, Dyes Pigment., 175, 108185 (2020)
  51. Hou J, Li M, Song Y, Angew. Chem.-Int. Edit., 57(10), 2544 (2018)
  52. Jiang K, Zhang L, Lu J, Xu C, Cai C, Lin H, Angew. Chem.-Int. Edit., 55(25), 7231 (2016)
  53. Kumari R, Sahu SK, Langmuir, 36(19), 5287 (2020)
  54. Tan HH, Gong G, Xie SW, Song Y, Zhang CF, Li N, Zhang D, Xu LJ, Xu JX, Zheng J, Langmuir, 35(35), 11503 (2019)
  55. Choi S, Lee SY, Kim DY, Park HK, Ko MJ, Cho KH, Choi J, J. Ind. Eng. Chem., 85, 226 (2020)
  56. Yoon B, Lee J, Park IS, Jeon S, Lee J, Kim JM, J. Mater. Chem. C, 1(13), 2388 (2013)
  57. Gao MX, Zou HY, Li YF, Huang CZ, Analyt. Chem., 89(3), 1808 (2017)
  58. Sanei M, Torabi S, Rad JK, Salehi-Mobarakeh H, Mahdavian AR, Mater. Chem. Phys., 240, 122126 (2020)
  59. Le Borgne B, Chung BY, Tas MO, King SG, Harnois M, Sporea RA, Electronics, 8(6), 699 (2019)
  60. Rad JK, Mahdavian AR, Khoei S, Shirvalilou S, ACS Appl. Mater. Interfaces, 10(23), 19483 (2018)
  61. Chen J, Zhong WB, Tang Y, Wu Z, Li Y, Yi PG, Jiang JH, Macromolecules, 48(11), 3500 (2015)
  62. Rad JK, Mahdavian AR, Khoei S, Esfahani AJ, Polymer, 98, 263 (2016)
  63. Tani S, Yamaki H, Nakayama D, Suzuki Y, Kawamata J, Clay Sci., 14(2), 81 (2009)
  64. Klajn R, Chem. Soc. Rev., 43(1), 148 (2014)
  65. Kang MY, Kim HS, Lee TH, Huh YH, KimYS, Park SJ, Jin JO, Lee PCW, Kwak MS, J. Ind. Eng. Chem., 80, 239 (2019)