Citation: JIN Qing-Jun, XU Min, HUANG Xin-Yi, LI Bo-Tian, WANG Ji-Shuai, KAN Cheng-You. Synthesis and Properties of Naphthalimide Fluorescent Dye and Covalent Fluorescent Polyurethane Emulsion[J]. Acta Physico-Chimica Sinica, 2015, 31(5): 989-997. doi: 10.3866/PKU.WHXB201503252
萘酰亚胺类荧光染料及共聚型荧光聚氨酯乳液的合成与性能
首先以4-溴-1,8-萘酐、2-氨基-1,3-丙二醇和甲醇钠为原料, 经亚胺化和取代两步反应合成出4-甲氧基-N-(2-羟基-1-羟甲基乙基)-1, 8-萘酰亚胺(MHHNA)活性荧光染料, 然后将其作为扩链剂通过相反转自乳化法制备出了共聚型荧光聚氨酯(PU) (PU-MHHNA)乳液, 并分别采用核磁共振氢谱(1H NMR)、核磁共振碳谱(13CNMR)、元素分析、傅里叶变换红外(FTIR)光谱、紫外-可见(UV-Vis)吸收光谱、荧光光谱、粒度分析、氙灯老化等方法对所得荧光染料的化学结构、PU乳液及乳胶膜的性能进行了表征. 结果表明, MHHNA和PU-MHHNA的荧光量子产率分别为0.73 和0.92, MHHNA的用量对所得PU乳液的胶体性质没有明显影响. PU-MHHNA的丙酮溶液在UV-Vis 吸收光谱上的最大吸收波长(λmax)为360.6 nm, 在荧光光谱上的最大激发波长(λex)和最大发射波长(λem)分别为362和435 nm. 随着温度的升高, PU-MHHNA的荧光强度逐渐降低. PU-MHHNA乳胶膜的耐光色牢度和耐溶剂色牢度均明显高于共混型荧光聚氨酯(PU/MBNA)乳胶膜.
English
Synthesis and Properties of Naphthalimide Fluorescent Dye and Covalent Fluorescent Polyurethane Emulsion
The reactive fluorescent dye 4- methoxy-N-(2- hydroxy- 1- hydroxymethylethyl) naphthalimide (MHHNA) was first synthesized by imidization and substitution reactions using 4-bromo-1,8-naphthalic anhydride, 2- amino- 1,3- propanediol, and sodium methoxide as initial materials. A series of covalent fluorescent polyurethane (PU) (PU-MHHNA) emulsions were then fabricated using MHHNA as the chain extender through a phase inverse self-emulsification process. The chemical structure of the synthesized fluorescent dyes and the properties of PU-MHHNA emulsions and their latex films were characterized by 1H nuclear magnetic resonance (1H NMR) spectroscopy, 13C nuclear magnetic resonance (13C NMR) spectroscopy, Fourier transform infrared (FTIR) spectroscopy, elemental analysis, ultraviolet- visible (UV- Vis) absorption spectroscopy, fluorescent spectroscopy, particle size analysis, and xenon arc aging measurements. The fluorescent quantum yields of MHHNA and PU-MHHNA were 0.73 and 0.92, respectively. The amount of MHHNA had no obvious influence on the colloidal properties of the PU-MHHNA emulsions. The maximum wavelength (λmax) of the UVVis absorption spectra was 360.6 nm, and fluorescent spectroscopy analysis indicated that the maximum excitation wavelength (λex) and maximum emission wavelength (λem) of PU-MHHNA in acetone were 362 and 435 nm, respectively. In addition, the fluorescence intensity of PU- MHHNA decreased with increasing temperature. The light fastness and solvent fastness of the PU-MHHNA film were much better than those of the non-covalent fluorescent polyurethane (PU/MBNA) film.
-
Key words:
-
Fluorescent dye
- / Polyurethane
- / Absorbance
- / Fluorescence intensity
- / Light fastness
-
-
[1]
(1) Kubo, H.; Yoshioka, N.; Takeuchi, T. Org. Lett. 2005, 7 (3), 359. doi: 10.1021/ol047992o
(1) Kubo, H.; Yoshioka, N.; Takeuchi, T. Org. Lett. 2005, 7 (3), 359. doi: 10.1021/ol047992o
-
[2]
(2) Fan, L. J.; Zhang, Y.; Jones, W. E., Jr. Macromolecules 2005, 38 (7), 2844. doi: 10.1021/ma047983v(2) Fan, L. J.; Zhang, Y.; Jones, W. E., Jr. Macromolecules 2005, 38 (7), 2844. doi: 10.1021/ma047983v
-
[3]
(3) Jiang, J. Q.; Tong, X.; Zhao, Y. J. Am. Chem. Soc. 2005, 127 (23), 8290.(3) Jiang, J. Q.; Tong, X.; Zhao, Y. J. Am. Chem. Soc. 2005, 127 (23), 8290.
-
[4]
(4) Fan, J.; Jiang, H. L.; Chen, D.; Zhu, K. J. J. Appl. Polym. Sci. 2006, 100 (2), 1214.(4) Fan, J.; Jiang, H. L.; Chen, D.; Zhu, K. J. J. Appl. Polym. Sci. 2006, 100 (2), 1214.
-
[5]
(5) Kim, J. M.; Chang, T. E.; Kang, J. H.; Park, K. H.; Han, D. K.; Ahn, K. D. Angew. Chem. Int. Edit. 2000, 39 (10), 1780. doi: 10.1002/(SICI)1521-3773(20000515)39:10<1780::AIDANIE1780> 3.0.CO;2-H(5) Kim, J. M.; Chang, T. E.; Kang, J. H.; Park, K. H.; Han, D. K.; Ahn, K. D. Angew. Chem. Int. Edit. 2000, 39 (10), 1780. doi: 10.1002/(SICI)1521-3773(20000515)39:10<1780::AIDANIE1780> 3.0.CO;2-H
-
[6]
(6) Lee, C.W.; Yuan, Z. Z.; Ahn, K. D.; Lee, S. H. Chem. Mater. 2002, 14 (11), 4572. doi: 10.1021/cm020016j(6) Lee, C.W.; Yuan, Z. Z.; Ahn, K. D.; Lee, S. H. Chem. Mater. 2002, 14 (11), 4572. doi: 10.1021/cm020016j
-
[7]
(7) Wang, W.; Wan, W.; Stachiw, A.; Li, A. D. Q. Biochemistry 2005, 44 (32), 10751.(7) Wang, W.; Wan, W.; Stachiw, A.; Li, A. D. Q. Biochemistry 2005, 44 (32), 10751.
-
[8]
(8) Wu, Z. Q.; ng, S. L.; Li, C.; Zhang, Z.; Huang, W. H.; Meng, L. Z.; Lu, X. J.; He, Y. B. Eur. Polym. J. 2005, 41 (9), 1985. doi: 10.1016/j.eurpolymj.2005.03.021(8) Wu, Z. Q.; ng, S. L.; Li, C.; Zhang, Z.; Huang, W. H.; Meng, L. Z.; Lu, X. J.; He, Y. B. Eur. Polym. J. 2005, 41 (9), 1985. doi: 10.1016/j.eurpolymj.2005.03.021
-
[9]
(9) Paiphansiri, U.; Dausend, J.; Musyanovych, A.; Mailander, V.; Landfester, K. Macromol. Biosci. 2009, 9 (6), 575. doi: 10.1002/mabi.v9:6(9) Paiphansiri, U.; Dausend, J.; Musyanovych, A.; Mailander, V.; Landfester, K. Macromol. Biosci. 2009, 9 (6), 575. doi: 10.1002/mabi.v9:6
-
[10]
(10) Zhou, J.; Zhang, X. Y.; Dai, J. B.; Li, J. P. J. Macromol. Sci. A 2012, 49 (10), 890. doi: 10.1080/10601325.2012.714684(10) Zhou, J.; Zhang, X. Y.; Dai, J. B.; Li, J. P. J. Macromol. Sci. A 2012, 49 (10), 890. doi: 10.1080/10601325.2012.714684
-
[11]
(11) Ramachandram, B.; Saroja, G.; Sankaran, N. B.; Samanta, A. J. Phys. Chem. B 2000, 104 (49), 11824. doi: 10.1021/jp000333i(11) Ramachandram, B.; Saroja, G.; Sankaran, N. B.; Samanta, A. J. Phys. Chem. B 2000, 104 (49), 11824. doi: 10.1021/jp000333i
-
[12]
(12) Grabchev, I.; Chovelon, J. M.; Qian, X. J. Photochem. Photobiol. A 2003, 158 (1), 37. doi: 10.1016/S1010-6030(03)00100-X(12) Grabchev, I.; Chovelon, J. M.; Qian, X. J. Photochem. Photobiol. A 2003, 158 (1), 37. doi: 10.1016/S1010-6030(03)00100-X
-
[13]
(13) Jin, R. Mol. Phys. 2013, 111 (24), 3793. doi: 10.1080/00268976.2013.793827(13) Jin, R. Mol. Phys. 2013, 111 (24), 3793. doi: 10.1080/00268976.2013.793827
-
[14]
(14) Wang, C. L.; Zhang, Z. J.; Chao, D. Y. J. Appl. Polym. Sci. 2003, 89 (10), 2723.(14) Wang, C. L.; Zhang, Z. J.; Chao, D. Y. J. Appl. Polym. Sci. 2003, 89 (10), 2723.
-
[15]
(15) Wang, C. L.; Zhang, Z. J.; Kuo, Y. M.; Chao, D. Y. Polym. Adv. Technol. 2004, 15 (1-2), 93.(15) Wang, C. L.; Zhang, Z. J.; Kuo, Y. M.; Chao, D. Y. Polym. Adv. Technol. 2004, 15 (1-2), 93.
-
[16]
(16) Chen, Y. C.; Chiou, R. R.; Huang, H. L.; Tsai, Y. Z.; Kuo, Y. M.; Chao, D. Y. J. Appl. Polym. Sci. 2005, 97 (2), 455.(16) Chen, Y. C.; Chiou, R. R.; Huang, H. L.; Tsai, Y. Z.; Kuo, Y. M.; Chao, D. Y. J. Appl. Polym. Sci. 2005, 97 (2), 455.
-
[17]
(17) Hu, X. H.; Zhang, X. Y.; Liu, J.; Dai, J. B. Polym. Int. 2014, 63 (3), 453. doi: 10.1002/pi.2014.63.issue-3(17) Hu, X. H.; Zhang, X. Y.; Liu, J.; Dai, J. B. Polym. Int. 2014, 63 (3), 453. doi: 10.1002/pi.2014.63.issue-3
-
[18]
(18) Ma, Y.; Tang, Q. Y.; Zhu, J.; Wang, L. H.; Yao, C. Chin. Chem. Lett. 2014, 25, 680. doi: 10.1016/j.cclet.2014.01.048(18) Ma, Y.; Tang, Q. Y.; Zhu, J.; Wang, L. H.; Yao, C. Chin. Chem. Lett. 2014, 25, 680. doi: 10.1016/j.cclet.2014.01.048
-
[19]
(19) Li, B. T.; Shen, J.; Liang, R. B.; Ji, W. J.; Kan, C. Y. Colloid Polym. Sci. 2012, 290 (18), 1893. doi: 10.1007/s00396-012-2718-7(19) Li, B. T.; Shen, J.; Liang, R. B.; Ji, W. J.; Kan, C. Y. Colloid Polym. Sci. 2012, 290 (18), 1893. doi: 10.1007/s00396-012-2718-7
-
[20]
(20) Li, B. T.; Shen, J.; Ji, W. J.; Cheng, G. Z.; Kan, C. Y. Chin. J. Chem. 2012, 30 (10), 2338. doi: 10.1002/cjoc.201200541(20) Li, B. T.; Shen, J.; Ji, W. J.; Cheng, G. Z.; Kan, C. Y. Chin. J. Chem. 2012, 30 (10), 2338. doi: 10.1002/cjoc.201200541
-
[21]
(21) Wu, R. H.; Zhao, H. Z.; Su, Q. D. J. Non-Cryst. Solids 2000, 278 (1-3), 223. doi: 10.1016/S0022-3093(00)00309-4(21) Wu, R. H.; Zhao, H. Z.; Su, Q. D. J. Non-Cryst. Solids 2000, 278 (1-3), 223. doi: 10.1016/S0022-3093(00)00309-4
-
[22]
(22) Xu, J. G.; Wang, Z. B. Fluorimetry, 3rd ed.; Science Press: Beijing, 2006; pp 56-57. [许金钩, 王尊本. 荧光分析法. 第三版. 北京: 北京科学出版社, 2006: 56-57.](22) Xu, J. G.; Wang, Z. B. Fluorimetry, 3rd ed.; Science Press: Beijing, 2006; pp 56-57. [许金钩, 王尊本. 荧光分析法. 第三版. 北京: 北京科学出版社, 2006: 56-57.]
-
[23]
(23) Costela, A.; Moreno, G. I.; Figuera, J. M. J. Appl. Phys. 1996, 80 (6), 3167. doi: 10.1063/1.363255(23) Costela, A.; Moreno, G. I.; Figuera, J. M. J. Appl. Phys. 1996, 80 (6), 3167. doi: 10.1063/1.363255
-
[24]
(24) Li, B. T.; Shen, J.; Jiang, Y. M.; Wang, J. S.; Kan, C. Y. J. Appl. Polym. Sci. 2013, 129 (3), 1484. doi: 10.1002/app.38848(24) Li, B. T.; Shen, J.; Jiang, Y. M.; Wang, J. S.; Kan, C. Y. J. Appl. Polym. Sci. 2013, 129 (3), 1484. doi: 10.1002/app.38848
-
[25]
(25) Grabchev, I.; Bojinov, V. Polym. Degrad. Stabil. 2000, 70 (2), 147. doi: 10.1016/S0141-3910(00)00100-2(25) Grabchev, I.; Bojinov, V. Polym. Degrad. Stabil. 2000, 70 (2), 147. doi: 10.1016/S0141-3910(00)00100-2
-
[26]
(26) Li, B. T.; Jiang, Y. M.; Wang, J. S.; Zhang, H.; Jin, Q. J.; Kan, C. Y. Acta Polym. Sin. 2013, No. 11, 1445. [李勃天, 江一明, 王吉帅, 张红, 金青君, 阚成友. 高分子学报, 2013, No. 11, 1445.]
(26) Li, B. T.; Jiang, Y. M.; Wang, J. S.; Zhang, H.; Jin, Q. J.; Kan, C. Y. Acta Polym. Sin. 2013, No. 11, 1445. [李勃天, 江一明, 王吉帅, 张红, 金青君, 阚成友. 高分子学报, 2013, No. 11, 1445.]
-
[1]
-
扫一扫看文章
计量
- PDF下载量: 222
- 文章访问数: 598
- HTML全文浏览量: 64
下载:
