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Synthesis and fluorescence properties of a waterborne polyurethane–acrylic hybrid polymeric dye

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Abstract

A waterborne polyurethane–acrylic hybrid polymeric dye was prepared depending on soap-free emulsion polymerization method. The resulting polymeric dye composed of methyl methacrylate (MMA) monomer which was polymerized into polymethyl methacrylate (PMMA) as cores and waterborne polyurethane-based dye was synthesized by anchoring dye monomers (6-amino-2-cyclohexyl-benz[de]isoquinone-1,3-dione) to polyurethane chains as shells. The average particle sizes of the hybrid polymeric dye emulsions were found to be increased with the increase in MMA contents for MMA monomers. Compared with dye monomers, the absorption intensities and fluorescence intensities of the hybrid polymeric dye were enhanced with the increase of particle sizes. This study revealed that enhanced fluorescence intensity of the hybrid polymeric dye was mainly attributed to the hindered formation of exciplexes among dye monomers and an augmented light absorption area. It was found that the fluorescence intensity of the hybrid polymeric dye was increased with increasing temperature and the trend first increased and then decreased with increase in concentration. Furthermore, the fluorescence of the hybrid polymeric dye emulsions was found to be very stable and not sensitive to the fluorescence quencher.

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References

  1. Yilmaz AH, Erdal C (2014) Barium hexaferrite reinforced polymeric dye composite coatings for radar absorbing applications. Polym Compos 35:602–610

    Article  Google Scholar 

  2. Gao Z, Zhang X, Chen Y (2015) Red fluorescence thin film based on a strong push–pull dicyanoisophorone system. Dyes Pigm 113:257–262

    Article  CAS  Google Scholar 

  3. Zhang XQ, Zhang XY, Yang B, Hui JF, Liu MY, Chi ZG, Liu SW, Xu JR, Wei Y (2014) A novel method for preparing AIE dye based cross-linked fluorescent polymeric nanoparticles for cell imaging. Polym Chem 5:683–688

    Article  CAS  Google Scholar 

  4. Chung YC, Choi JW, Lee HL, Chun BC (2014) The characterization and effects of the alizarin series dyes grafted to polyurethane copolymers on the photoluminescence and low temperature flexibility. Fiber Polym 15:8–17

    Article  CAS  Google Scholar 

  5. Chung YC, Yang K, Choi JW, Chun BC (2014) Characterisation and application of polyurethane copolymers grafted with photoluminescent dyes. Color Technol 130:305–313

    Article  CAS  Google Scholar 

  6. Ali P, Malihe D, Mohadese D (2014) Adsorption characteristics of malachite green dye onto novel kappa-carrageenan-g-polyacrylic acid/TiO2–NH2 hydrogel nanocomposite. J Iran Chem Soc 11:1057–1065

    Article  Google Scholar 

  7. Jang SP, Choi MJ, Vittal R, Kim KJ (2007) Anchorage of N3 dye-linked polyacrylic acid to TiO2/electrolyte interface for improvement in the performance of a dye-sensitized solar cell. Sol Energy Mater Sol C 91:1209–1214

    Article  CAS  Google Scholar 

  8. Guyot A, Landfester K, Schork FJ, Wang C (2007) Hybrid polymer latexes. Prog Polym Sci 32:1439–1461

    Article  CAS  Google Scholar 

  9. Jiang XB, Zhu XL, Zhang ZG, Kong XZ, Tan YB (2011) Determination of crosslinking and grafting in polyurethane–acrylic hybrid material and their theoretical calculations. Chem Res Chin Univ 27:154–157

    CAS  Google Scholar 

  10. Jiang XB, Kong XZ, Zhu XL, Zhang Z, Zhang ZG (2010) Calculation of grafting and property characterization in polyurethane–acrylic hybrid materials prepared by emulsion process. Macromol Chem Phys 211:2201–2210

    Article  CAS  Google Scholar 

  11. Ko HW, Chi MH, Chang CW, Chu CW, Luo KH, Chen JT (2015) Fabrication of core-shell polymer nanospheres in the nanopores of anodic aluminum oxide templates using polymer blend solutions. ACS Macro Lett 4:717–720

    Article  CAS  Google Scholar 

  12. Reddy KR, Hassan M, Gomes VG (2015) Hybrid nanostructures based on titanium dioxide for enhanced photo catalysis. Appl Catal A Gen 489:1–16

    Article  CAS  Google Scholar 

  13. Reddy KR, Lee KP, Gopalan AI (2008) Self-assembly approach for the synthesis of electro-magnetic functionalized Fe3O4/polyaniline nanocomposites: effect of dopant on the properties. Colloids Surf A Physicochem Eng Asp 320:49–56

    Article  CAS  Google Scholar 

  14. Hassan M, Reddy KR, Haque E, Faisal SN, Ghasemi S, Minett AI, Gomes VG (2014) Hierarchical assembly of graphene/polyaniline nanostructures to synthesize free-standing supercapacitor electrode. Compos Sci Technol. 98:1–8

    Article  CAS  Google Scholar 

  15. Zhang YP, Lee SH, Reddy KR, Gopalan AI, Lee KP (2007) Synthesis and characterization of core-shell SiO2 nanoparticles/poly(3-aminophenylboronic acid) composites. J Appl Polym Sci 104:2743–2750

    Article  CAS  Google Scholar 

  16. Reddy KR, Sin BC, Yoo CH, Sohn D, Lee Y (2009) Coating of multiwalled carbon nanotubes with polymer nanospheres through microemulsion polymerization. J Colloid Interface Sci 340:160–165

    Article  CAS  Google Scholar 

  17. Hassan M, Reddy KR, Haque E, Minett AI, Gomes VG (2013) High-yield aqueous phase exfoliation of graphene for facile nanocomposite synthesis via emulsion polymerization. J Colloid Interface Sci 410:43–51

    Article  CAS  Google Scholar 

  18. Reddy KR, LeeK P, Gopalan AI, Kimms Showkat A, Nho YC (2006) Synthesis of metal (Fe or Pd)/alloy (Fe–Pd)-nanoparticles-embedded multiwall carbon nanotube/sulfonated polyaniline composites by γ irradiation. Polym Sci Part A 44:3355–3364

    Article  CAS  Google Scholar 

  19. Lee YR, Kim SC, Lee H, Jeong HM, Raghu AV, Reddy KR, Kim BK (2011) Graphite oxides as effective fire retardants of epoxy resin. Macromol Res 19:66–71

    Article  CAS  Google Scholar 

  20. Reddy Kakarla Raghava, Lee Kwang-Pill, Gopalan Anantha Iyenger (2007) Self-assembly directed synthesis of poly(ortho-toluidine)-metal(gold and palladium) composite nanospheres. J Nanosci Nanotechnol 7:3117–3125

    Article  CAS  Google Scholar 

  21. Zhang JF, Li XF, Shi XH, Hua M, Zhou XP, Wang XQ (2012) Synthesis of core–shell acrylic–polyurethane hybrid latex as binder of aqueous pigment inks for digital inkjet printing. Prog Nat Sci Mater Int 22:71–78

    Article  Google Scholar 

  22. Lopez A, Degrandi E, Canetta E, Keddie JL, Creton C, Asua JM (2011) Simultaneous free radical and addition miniemulsion polymerization: effect of the diol on the microstructure of polyurethane–acrylic pressure-sensitive adhesives. Polymer 52:3021–3030

    Article  CAS  Google Scholar 

  23. Nicholas B, Paula C, Jose MA (2013) Effect of reaction temperature on adhesive properties of waterborne polyurethane/acrylic hybrids synthesized by semicontinuous miniemulsion polymerization. Macromol Res 21:709–718

    Article  Google Scholar 

  24. Daniloska V, Tomovskaa R, Asua JM (2012) Hybrid miniemulsion photopolymerization in a continuous tubular reactor-a way to expand the characteristics of polyurethane/acrylics. Chem Eng J 184:308–314

    Article  CAS  Google Scholar 

  25. Liu Z, Jones FR, Zhai Z (2014) Interfacial adhesion of polyamide 66 fibres to an aqueous polyurethane–acrylic hybrid polymer adhesive. J Adhes 90:310–326

    Article  CAS  Google Scholar 

  26. Wang CP, Chu FX, Jin LW, Lin MT, Xu YZ, Guyot (2009) A Polyurethane–acrylate hybrid latexes from miniemulsion polymerization: effect of endgroups on structure and properties. Polym Adv Technol 20:319–326

    Article  Google Scholar 

  27. Reddy KR, Raghu AV, Jeong HM, Siddaramaiah (2009) Synthesis and characterization of pyridine-based polyurethanes. Des Monomers Polym 12:109–118

    Article  CAS  Google Scholar 

  28. Reddy KR, Raghu AV, Jeong HM (2008) Synthesis and characterization of novel polyurethanes based on 4,4′-{1,4-phenylenebis[methylylidenenitrilo]}dipheno]. Polym Bull 60:609–616

    Article  CAS  Google Scholar 

  29. Hu XH, Zhang XY, Liu J, Dai JB (2013) Synthesis, characterization and fluorescence performance of a waterborne polyurethane-based polymeric dye. J Lumin 142:23–37

    Article  CAS  Google Scholar 

  30. Du FS, Zhou Y, Li ZC, Li FM (2000) Vinyl monomers bearing chromophore moieties and their polymers. XII. Synthesis and fluorescence behavior of vinyloxy monomers having 1,8-naphthalimide moiety with different spacer lengths and their polymers. Polym Adv Technol 11:798–804

    Article  CAS  Google Scholar 

  31. Hu XH, Zhang XY, Liu J, Dai JB (2014) Synthesis, characterization and fluorescence performance of a waterborne polyurethane-based fluorescent dye WPU-ACN. Polym Int 63:453–458

    Article  CAS  Google Scholar 

  32. Schoth A, Landfester K, Muñoz-Espí R (2015) Surfactant-free polyurethane nanocapsules via inverse pickering miniemulsion. Langmuir 31:3784–3788

    Article  CAS  Google Scholar 

  33. Hassan M, Haque E, Kr Reddy, Minett Andrew I, Chen J, Gomes VG (2014) Edge-enriched graphene quantum dots for enhanced photo-luminescence and supercapacitance. Nanoscale 6:11988–11994

    Article  CAS  Google Scholar 

  34. Reddy KR, Jeong HM, Lee Y, Raghu AV (2010) Synthesis of MWCNTs-core/thiophene polymer-sheath composite nanocables by a cationic surfactant-assisted chemical oxidative polymerization and their structural properties. Polym Sci Part A 48:1477–1484

    Article  CAS  Google Scholar 

  35. Reddy KR, Lee KP, Kim JY, Lee Y (2008) Self-assembly and graft polymerization route to monodispersed Fe3O4@SiO2-polyaniline core-shell composite nanoparticles: physical properties. J Nanosci Nanotechnol 8:5632–5639

    Article  CAS  Google Scholar 

  36. Hu XH, Zhang XY, Dai JB, Liu J (2011) Synthesis and fluorescent investigations of VBL-based waterborne polyurethane dye. J Lumin 131:2160–2165

    Article  CAS  Google Scholar 

  37. Li Z, Dong YQ, Mi BX, Tang YH, Häussler M, Tong H, Dong YP, Lam JWY, Ren Y, Sung HHY, Wong KS, Gao P, Williams ID, Kwok HS, Tang BZ (2005) Structural control of the photoluminescence of silole regioisomers and their utility as sensitive regiodiscriminating chemosensors and efficient electroluminescent materials. J Phys Chem B 109:l006l–10066

    Google Scholar 

  38. Kawa M, Fréochet JMJ (1998) Self-assembled lanthanide-cored dendrimer complexes: enhancement of the luminescence properties of lanthanide ions through site-isolation and antenna effects. Chem Mater 10:286–296

    Article  CAS  Google Scholar 

  39. Virtanen J, Lemmetyinen H, Tenhu H (2001) Fluorescence and EPR studies on the collapse of poly(N-isopropyl acrylamide)-g-poly(ethylene oxide) in water. Polymer 42:9487–9493

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Financial supports from the National Natural Science Foundation of China (No. 51573001), China Postdoctoral Science Foundation (No. 2015M571923), the Natural Science Foundation of Anhui Province (No. 1508085MB36), and the Natural Science Foundation of Anhui Education Department (No. KJ2014A045) are acknowledged.

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Authors and Affiliations

  1. School of Materials and Chemical Engineering, Anhui Jianzhu University, Hefei, 230022, China

    Xianhai Hu, Jin Liu, Yao Deng & Congliang Cheng

  2. College of Chemistry and Engineering, Hefei University of Technology, Hefei, 230009, China

    Xianhai Hu & Yunsheng Ding

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  1. Xianhai Hu
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  2. Yunsheng Ding
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  3. Jin Liu
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  4. Yao Deng
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Correspondence to Xianhai Hu or Yunsheng Ding.

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Hu, X., Ding, Y., Liu, J. et al. Synthesis and fluorescence properties of a waterborne polyurethane–acrylic hybrid polymeric dye. Polym. Bull. 74, 555–569 (2017). https://doi.org/10.1007/s00289-016-1729-9

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  • DOI: https://doi.org/10.1007/s00289-016-1729-9

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