Abstract
Novel waterborne polyurethane (WPU) with side-chained Phenylazonaphthalene group was prepared by step-growth addition polymerization between isophorone diisocyanate (IPDI), polytetramethylene ether glycol (PTMG), 2, 2-dimethylol propionic acid (DMPA) and a self-made azo diol, N,N-(2-hydroxyethyl)-4-phenylazo naphthylamine (HPN), as a chain extender to partially substitute for 1, 4-butanediol (BDO). 1H nuclear magnetic resonance spectra (1H NMR), Fourier transform infrared spectroscopy (FTIR) and Ultraviolet–Visible (UV–Vis) spectroscopy were used to research the properties of HPN and HPN-WPU. The WPU latex presented obvious trans–cis photoisomerization during UV radiation and the absorption wavelength of the HPN exhibited a blue shift after attached into polyurethane chains. It needed longer irradiated time to finish isomerization due to the emulsion aggregated states, comparing with phenylazonaphthalene monomer solution and WPU dilute solution.
Similar content being viewed by others
References
Spiridon MC, Iliopoulos K, Jerca FA, Jerca VV, Vuluga DM, Vasilescu DS, Gindre D, Sahraoui B (2015) Novel pendant azobenzene/polymer systems for second harmonic generation and optical data storage. Dyes Pigm 114:24–32
Yan P, Wang K, Cui P, Gao J, Ma J, Zhang Q (2015) Single-exposure polarization phase-shifting interferometer using an azo-polymer orientation array. Opt Lasers Eng 73:75–79
Yesodha SK, Pillai CKS, Tsutsumi N (2004) Stable polymeric materials for nonlinear optics: a review based on azobenzene systems. Prog Polym Sci 29(1):45–74
Kundu S, Lee MH, Lee SH, Kang SW (2013) In situ homeotropic alignment of nematic liquid crystals based on photoisomerization of azo-dye, physical adsorption of aggregates, and consequent topographical modification. Adv Mater 25(24):3365–3370
Liu J, Bu W, Pan L, Shi J (2013) NIR-triggered anticancer drug delivery by upconverting nanoparticles with integrated azobenzene-modified mesoporous silica. Angew Chem Int Ed 52(16):4375–4379
Samui AB, Pandey S, Mishra SP (2015) Main chain photoresponsive liquid crystalline polymer synthesized through hydrosilylation. RSC Advances 5(84):68351–68355
Wang F, Wu M, Wang Y, Yu Y, Wu X, Zhuge L (2013) Influence of thickness and annealing temperature on the electrical, optical and structural properties of AZO thin films. Vacuum 89:127–131
Zhang D, Fan Y, Li H, Li K, Yao Y, Zhou Y, Yan D (2015) A dumbbell-like supramolecular triblock copolymer and its self-assembly of light-responsive vesicles. RSC Advances 5(59):47762–47765
Lee CK, Beiermann BA, Silberstein MN, Wang J, Moore JS, Sottos NR, Braun PV (2013) Exploiting force sensitive spiropyrans as molecular level probes. Macromolecules 46(10):3746–3752
Lee CK, Davis DA, White SR, Moore JS, Sottos NR, Braun PV (2010) Force-induced redistribution of a chemical equilibrium. J Am Chem Soc 132(45):16107–16111
Li J, Ma L, Chen G, Zhou Z, Li Q (2015) A high water-content and high elastic dual-responsive polyurethane hydrogel for drug delivery. J Mater Chem B 3(42):8401–8409
Sekkat Z, Yasumatsu D, Kawata S (2002) Pure photoorientation of azo dye in polyurethanes and quantification of orientation of spectrally overlapping isomers. J Phys Chem B 106(48):12407–12417
Wu X, Liu L, Fang W, Qiao C, Li T (2016) Effect of hard segment architecture on shape memory properties of polycaprolactone-based polyurethane containing azobenzene. J Mater Sci 51(5):2727–2738
Zhang Y, Wang C, Pei X, Wang Q, Wang T (2010) Shape memory polyurethanes containing azo exhibiting photoisomerization function. J Mater Chem 20(44):9976–9981
Kim BK, Lee JC (1996) Waterborne polyurethanes and their properties. J Polym Sci, Part A: Polym Chem 34(6):1095–1104
Li J, Zhang X, Liu Z, Li W, Dai J (2015) Studies on waterborne polyurethanes based on new medium length fluorinated diols. J Fluorine Chem 175:12–17
Madbouly SA, Xia Y, Kessler MR (2013) Rheological behavior of environmentally friendly castor oil-based waterborne polyurethane dispersions. Macromolecules 46(11):4606–4616
Hu X, Zhang X, Liu J (2015) Synthesis and optical performances of a waterborne polyurethane-based polymeric dye. Int J Polym Sci 2015
Li J, Zhang X, Gooch J, Sun W, Wang H, Wang K (2015) Photo-and pH-sensitive azo-containing cationic waterborne polyurethane. Polym Bull 72(4):881–895
Rafiemanzelat F, Adli V, Mallakpour S (2015) Effective preparation of clay/waterborne Azo-containing polyurethane nanocomposite dispersions incorporated anionic groups in the chain termini. Des Monomers Polym 18(4):303–314
Zheng Y, Zhang X, Li J (2015) Synthesis and photochromism properties of anionic waterborne polyurethane containing azobenzene chromophores. J Macromol Sci Part A 52(11):942–949
ASTM D2572-97 (2010) Standard test method for isocyanate groups in urethane materials or prepolymers. ASTM International, West Conshohocken, PA. http://www.astm.org
Bai CY, Zhang XY, Dai JB, Li WH (2006) A new UV curable waterborne polyurethane: effect of C C content on the film properties. Prog Org Coat 55(3):291–295
Zhou C, Xie T, Zhou R, Trindle CO, Tikman Y, Zhang X, Zhang G (2015) Waterborne polyurethanes with tunable fluorescence and room-temperature phosphorescence. ACS Appl Mater Interfaces 7(31):17209–17216
Kondo T, Yoshii K, Horie K, Itoh M (2000) Photoprobe study of siloxane polymers. 3. Local free volume of polymethylsilsesquioxane probed by photoisomerization of azobenzene. Macromolecules 33(10):3650–3658
Xie S, Natansohn A, Rochon P (1993) Recent developments in aromatic azo polymers research. Chem Mater 5(4):403–411
Acknowledgements
This work was supported by National High Technology Research and Development Program of China (No.2015AA033903).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Sun, W., Zheng, Y. & Zhang, X. Photoisomerization of waterborne polyurethane with side-chained phenylazonaphthalene group. Polym. Bull. 74, 3109–3121 (2017). https://doi.org/10.1007/s00289-016-1895-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-016-1895-9