Skip to main content
SpringerLink
Log in

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

  • Published:
Journal of Coatings Technology and Research Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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. 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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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. 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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Google Scholar 

  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)

    Google Scholar 

  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)

    Article  Google Scholar 

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

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

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

  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)

    Article  Google Scholar 

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

    Google Scholar 

  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)

    Article  Google Scholar 

Download references

Acknowledgments

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

Author information

Authors and Affiliations

  1. Department of Chemical Engineering and Key Laboratory of Advanced Materials of Ministry of Education, Tsinghua University, Beijing, 100084, People’s Republic of China

    Qingjun Jin, Yang Hu, Jie Shen, Botian Li & Chengyou Kan

Authors
  1. Qingjun Jin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yang Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jie Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Botian Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Chengyou Kan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chengyou Kan.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 382 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

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

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11998-016-9874-5

Keywords

Search

Navigation