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A novel 1,8-naphthalimide green fluorescent dye and its corresponding intrinsically fluorescent polyurethane latexes

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Abstract

A novel green fluorescent dye, 4-hexylamino-N-(2-hydroxy-1-hydroxymethylethyl)-1,8-naphthalimide (AHHNA), was designed and synthesized, and then used as a chain extender to prepare a series of intrinsically green fluorescent polyurethane (PU) latexes. The chemical structure of AHHNA and the properties of the fluorescent PU latexes and their films were characterized. It was found that the UV–Vis and the fluorescent spectra of the PUs remained fairly consistent with AHHNA, and the fluorescence emitting capacity of 1,8-naphthalimide group was enhanced by covalently bonding AHHNA onto the PU chain. The amount of AHHNA used in the latex preparation had no obvious effect on the latex colloid properties including particle size, poly index, and zeta potential. Results showed that the color difference (ΔE) and the extraction rate (R e) of the intrinsically fluorescent PU latex film were 5.72% and 3.1%, respectively, while the ΔE and R e of the extrinsically fluorescent PU latex film were 8.31% and 84.7%, respectively, indicating that the light fastness and the solvent fastness of the intrinsically fluorescent PU latex film were much better than those of the extrinsically fluorescent PU latex film.

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References

  1. 1.

    Kubo, H, Yoshioka, N, Takeuchi, T, “Fluorescent Imprinted Polymers Prepared with 2-Acrylamidoquinoline as a Signaling Monomer.” Org. Lett., 7 (3) 359–362 (2005)

  2. 2.

    Wu, Z-Q, Gong, S-L, Li, C, Zhang, Z, Huang, W-H, Meng, L-Z, Lu, X-J, “Novel Water-Soluble Fluorescent Polymer Containing Recognition Units: Synthesis and Interactions with PC12 Cell.” Eur. Polym. J., 41 (9) 1985–1992 (2005)

  3. 3.

    Fan, J, Jiang, H-L, Chen, D, Zhu, K-J, “The Effect of Substitution Levels on the Luminescent and Degradation Properties of Fluorescent Poly(ester-anhydride)s.” J. Appl. Polym. Sci., 100 (2) 1214–1221 (2006)

  4. 4.

    Bojinov, V, Grabchev, I, “A New Method for Synthesis of 4-Allyloxy-1,8-naphthalimide Derivatives for Use as Fluorescent Brighteners.” Dyes Pigments, 51 (1) 57–61 (2001)

  5. 5.

    Campo, LF, Rodembusch, FS, Stefani, V, “New Fluorescent Monomers and Polymers Displaying an Intramolecular Proton-Transfer Mechanism in the Electronically Excited State (ESIPT). IV. Synthesis of Acryloylamide and Diallylamino Benzazole Dyes and Its Copolymerization with MMA.” J. Appl. Polym. Sci., 99 (5) 2109–2116 (2006)

  6. 6.

    Lee, CW, Yuan, Z-Z, Ahn, KD, Lee, SH, “Color and Fluorescent Imaging of t-BOC-Protected Quinizarin Methacrylate Polymers.” Chem. Mater., 14 (11) 4572–4575 (2002)

  7. 7.

    Garcia-Pacios, V, Costa, V, Colera, M, Martin-Martinez, JM, “Waterborne Polyurethane Dispersions Obtained with Polycarbonate of Hexanediol Intended for Use as Coatings.” Prog. Org. Coat., 71 (2) 136–146 (2011)

  8. 8.

    Li, X-J, Hu, J, Sun, D-X, Zhang, Y-H, “Nanosilica Reinforced Waterborne Siloxane-Polyurethane Nanocomposites Prepared Via ‘Click’ Coupling.” J. Coat. Technol. Res., 11 (4) 517–531 (2014)

  9. 9.

    Yu, Y-T, Wang, J, “Synthesis and Properties of Block and Graft Waterborne Polyurethane Modified with α, ω-Bis(3-(1-methoxy-2-hydroxypropoxy)propyl)polydimethylsiloxane and α-N, N-Dihydroxyethylaminopropyl-ω-butylpolydimethylsiloxane.” Polym. Eng. Sci., 54 (4) 805–811 (2014)

  10. 10.

    Zhang, S-W, Chen, J-F, Han, D, Feng, Y-Q, Shen, C, Chang, C, Song, Z-L, Zhao, J, “Effect of Polyether Soft Segments on Structure and Properties of Waterborne UV-curable Polyurethane Nanocomposites.” J. Coat. Technol. Res., 12 (3) 563–569 (2015)

  11. 11.

    Yang, J, Fu, Y, Zhao, Z-L, Tian B-C, “Waterborne Anti-fake Stamp-pad Ink.” Chinese Patents CN 101,921,507 A, 2010

  12. 12.

    Hu, X-H, Zhang, X-Y, Dai, J-B, “Synthesis and Characterization of a Novel Waterborne Stilbene-Based Polyurethane Fluorescent Brightener.” Chin. Chem. Lett., 22 (8) 997–1000 (2011)

  13. 13.

    Zhou, J, Zhang, X-Y, Dai, J-B, Li, J-P, “Synthesis and Fluorescent Performance of Fluorescein-Functionalized Waterborne Polyurethane.” Macromol. Sci. Pure Appl. Chem., 49 (10) 890–896 (2012)

  14. 14.

    Hu, X-H, Zhang, X-Y, Liu, J, “Synthesis and Optical Performances of a Waterborne Polyurethane-based Polymeric Dye.” Int. J. Polym. Sci., Article ID 425083 (2015)

  15. 15.

    Qian, X-H, Zhu, Z-H, Chen, K-C, “The Synthesis, Application and Prediction of Stokes Shift in Fluorescent Dyes Derived from 1,8-Naphthalic Anhydride.” Dyes Pigments, 11 (1) 13–20 (1989)

  16. 16.

    Gruzinskii, VV, Kukhto, AV, Shakkakh, GK, “Spectra of Lasing Efficiency in Lasers with Solutions of Complex Organic Compounds.” J. Appl. Spectrosc., 65 (3) 463–465 (1998)

  17. 17.

    Georgiev, NI, Bojinov, VB, Marinova, N, “Novel PAMAM Light-harvesting Antennae Based on 1,8-Naphthalimide: Synthesis, Energy Transfer, Photophysical and pH Sensing Properties.” Sens. Actuators B Chem., 150 (2) 655–666 (2010)

  18. 18.

    Yin, H, Zhu, W-P, Xu, Y-F, Dai, M, Qian, X-H, Li, Y-L, Liu, J-W, “Novel Aliphatic N-Oxide of Naphthalimides as Fluorescent Markers for Hypoxic Cells in Solid Tumor.” Eur. J. Med. Chem., 46 (7) 3030–3037 (2011)

  19. 19.

    Zhang, Y-Y, Zhou, C-H, “Synthesis and Activities of Naphthalimide Azoles as a New Type of Antibacterial and Antifungal Agents.” BioOrg. Med. Chem. Lett., 21 (14) 4349–4352 (2011)

  20. 20.

    Ma, Y, Tang, Q-Y, Zhu, J, Wang, L-H, Yao, C, “Fluorescent and Thermal Properties of Siloxane-polyurethanes Based on 1,8-Naphthalimide.” Chin. Chem. Lett., 25 (5) 680–686 (2014)

  21. 21.

    Wang, C-L, Zhang, Z-J, Yang, C-Y, Chao, D-Y, “Study of Fluorescence from Fluorescent Dye-Based Polyurethane Ionomer.” J. Appl. Polym. Sci., 89 (10) 2723–2737 (2003)

  22. 22.

    Wang, C-L, Zhang, Z-J, Kuo, Y-M, Chao, D-Y, “Fluorescence from Fluorescent Dye-Based Polyurethane Ionomer (II).” Polym. Adv. Technol., 15 (1–2) 93–99 (2004)

  23. 23.

    Chen, Y-C, Chiou, RR, Huang, H-L, Tsai, Y-Z, Kuo, Y-M, Chao, D-Y, “Fluorescence from Fluorescent Dye Based Polyurethane Ionomer (III).” J. Appl. Polym. Sci., 97 (2) 455–465 (2005)

  24. 24.

    Hu, X-H, Zhang, X-Y, Liu, J, Dai, J-B, “Synthesis, Characterization and Fluorescence Performance of a Saterborne Polyurethane-Based Fluorescent Dye 4-Amino-N-cyclohexyl-1,8-naphthalimide, WPU-CAN.” Polym. Int., 63 (3) 453–458 (2014)

  25. 25.

    Wang, J-X, Kan, C-Y, Liu, D-S, “Synthesis of Novel Monomeric Dyes with Anthraquinone Residue.” Chin. Chem. Lett., 15 (10) 1161–1163 (2004)

  26. 26.

    Li, B-T, Shen, J, Liang, R-B, Ji, W-J, Kan, C-Y, “Synthesis and Characterization of Covalently Colored Polymer Latex Based on New Polymerizable Anthraquinone Dyes.” Colloid Polym. Sci., 290 (18) 1893–1900 (2012)

  27. 27.

    Li, B-T, Shen, J, Jiang, Y-M, Wang, J-S, Kan, C-Y, “Preparation and Properties of Covalently Colored Polymer Latex Based on a New Anthraquinone Monomer.” J. Appl. Polym. Sci., 129 (3) 1484–1490 (2013)

  28. 28.

    Jin, Q-J, Xu, M, Huang, X-Y, Li, B-T, Wang, J-S, Kan, C-Y, “Synthesis and Properties of Naphthalimide Fluorescent Dye and Covalent Fluorescent Polyurethane Emulsion.” Acta Phys. Chim. Sin., 31 (5) 989–997 (2015)

  29. 29.

    Jin, Q-J, Li, B-T, Wang, J-S, Shen, J, Hu, Y, Kan, C-Y, “Preparation and Properties of an Anthraquinone Blue Chain Extender and Blue Polyurethane-acrylate Latex Prepared Using the Chain Extender.” Acta Polym. Sin., 5 610–616 (2015)

  30. 30.

    Wang, J-S, Li, B-T, Jin, Q-J, Huang, X-Y, Shen, J, Kan, C-Y, “Preparation of Covalently Colored Polymer Latex through Miniemulsion Polymerization Based on a Polymerizable Dye.” Des. Monomers Polym., 18 (7) 611–619 (2015)

  31. 31.

    ASTMD Standard, Standard Test Method for Isocyanate Groups in Urethane Materials or Prepolymers, pp. 2572–2797. ASTM, West Conshohocken, PA, USA, 2010

  32. 32.

    Demas, JN, Crosby, GA, “The Measurement of Photoluminescence Quantum Yields.” J. Phys. Chem., 75 (8) 991–1023 (1971)

  33. 33.

    Loutfy, RO, “Fluorescence Probes for Polymerization Reactions: Bulk Polymerization of Styrene, n-Butyl Methacrylate, Ethyl Methacrylate, and Ethyl Acrylate.” J. Polym. Sci. Pol. Phys., 20 (5) 825–835 (1982)

  34. 34.

    Wu, R-H, Zhao, H-Z, Su, Q-D, “Photoacoustic and Fluorescence Studies of Silica Gels Doped With Rare Earth Salicylic Acid Complexes.” J. Non-Cryst. Solids, 278 (1–3) 223–227 (2000)

  35. 35.

    Li, F-M, Chen, S-J, Li, Z-C, Qiu, J, “Vinyl Monomers Bearing Chromophore Moieties and Their Polymers. I. Initiation and Photochemical Behavior of N-acryloyl-N′-phenylpiperazines and Their Polymers.” J. Polym. Sci. Polym. Chem., 34 (10) 1881–1888 (1996)

  36. 36.

    Qiu, J, Li, Z-C, Gao, Q-Y, Yao, G-Q, Yang, G-X, Zhang, J-X, Li, F-M, “Vinyl Monomers Bearing Chromophore Moieties and Their Polymers. III. Synthesis and Photochemical Behavior of Acrylic Monomers Having Phenothiazine Moieties and Their Polymers.” J. Polym. Sci. Polym. Chem., 34 (14) 3015–3023 (1996)

  37. 37.

    Zhang, L-Y, Zhuang, D-H, He, J-X, “Color Fastness to Perspiration-Light of Reactive Dyeings.” Dye. Finish., 11 35–38 (2005)

  38. 38.

    Grabchev, I, Bojinov, V, “Synthesis and Characterisation of Fluorescent Polyacrylonitrile Copolymers with 1,8-Naphthalimide Side Chains.” Polym. Degrad. Stab., 70 (2) 147–153 (2000)

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Acknowledgments

The authors are grateful to the support of the National Basic Research Program of China (No. 2014CB932202).

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Correspondence to Chengyou Kan.

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Jin, Q., Hu, Y., Shen, J. et al. A novel 1,8-naphthalimide green fluorescent dye and its corresponding intrinsically fluorescent polyurethane latexes. J Coat Technol Res 14, 571–582 (2017). https://doi.org/10.1007/s11998-016-9874-5

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Keywords

  • Fluorescent chain extender
  • PU latex
  • Green
  • Color difference
  • Fastness