Top

Journal of Coatings Technology and Research

Published in:

24-02-2017

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

Authors: Qingjun Jin, Yang Hu, Jie Shen, Botian Li, Chengyou Kan

Published in: Journal of Coatings Technology and Research | Issue 3/2017

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

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.

previous article Transparent UV-cured clay/UV-based nanocomposite coatings on wood substrates: surface roughness and effect of relative humidity on optical properties

next article Investigation of cardanol-based reactive polyamide as a crosslinker in epoxy zinc-rich primer

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

Available only for authorised users

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

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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.

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)CrossRef

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)CrossRef

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.

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.

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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)CrossRef

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.

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)CrossRef

Title: A novel 1,8-naphthalimide green fluorescent dye and its corresponding intrinsically fluorescent polyurethane latexes
Authors: Qingjun Jin
Yang Hu
Jie Shen
Botian Li
Chengyou Kan
Publication date: 24-02-2017
Publisher: Springer US
Published in: Journal of Coatings Technology and Research / Issue 3/2017
Print ISSN: 1547-0091
Electronic ISSN: 1935-3804
DOI: https://doi.org/10.1007/s11998-016-9874-5

Springer Professional

Abstract

Please log in to get access to your license.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Other articles of this Issue 3/2017

Epoxy-based paints from glycolysis products of postconsumer PET bottles: synthesis, wet paint properties and film properties

Boehmite/methacrylic nano-composites as protective coatings for natural stones: comparison between sunlight and UV photopolymerization cure reaction

Inhibitors for prolonging corrosion protection of Mg-rich primer on Al alloy 2024-T3

Investigation of cardanol-based reactive polyamide as a crosslinker in epoxy zinc-rich primer

Refinement of solid layers via wetting on homogeneous lyophilic surfaces

Microwave-assisted preparation of photoactive TiO2 on textile substrates

Premium Partners