Abstract
The present study investigates new polyurethanes with improved stability to UV radiation by the inclusion of azobenzene side groups on the polymer main chain. These polyurethanes were prepared from a prepolymer (polycaprolactone diol and 1,6-hexamethylene diisocyanate) with 2,4-dihydroxyazobenzene (Sudan Orange G) as a chain extender. A polyurethane chain-extended with 1,4-butanediol was prepared for comparison. The paper studies how the amount and structure of the chain extenders affect the polymer structure and the mechanical, surface and thermal properties of the obtained polyurethanes, before and after subjection to UV irradiation, All the synthesized polyurethanes showed good thermal stability up to 250 ºC. In terms of mechanical properties, the samples exhibit good tensile strength and elongation at break. The surface contact angle increases with chain extender content and UV exposure time. The inclusion of azobenzene groups into the polyurethane main chain makes these polyurethanes appropriate for use in colored polymer materials with good UV radiation stability.
Similar content being viewed by others
References
Engels H-W, Pirkl H-G, Albers R, Albach RW, Krause J, Hoffmann A, Casselmann H, Dormish J (2013) Polyurethanes: Versatile materials and sustainable problem solvers for today’s challenges. Angew Chem Int Ed 52:9422–9441
Oprea S, Potolinca VO, Oprea V (2020) Synthesis and characterization of novel polyurethane elastomers that include curcumin with various cross-linked structures. J Polym Res 27:60
Chen HM, Li XP, Chen J, He XD, Huang WM, Zhu K, Yu WH, Ni HL, Zhao KQ, Hu P (2021) Unified method to prepare thermoplastic/thermoset soft polyurethanes reshape-able around room temperature on-demand. J Polym Res 28:201
Boisaubert P, Kebir N, Schuller A-S, Burel F (2020) Photo-crosslinked coating from an acrylate terminated non-isocyanate polyurethane (NIPU) and reactive diluent. Eur Polym J 138:109961
Doley S, Bora A, Saikia P, Ahmed S, Dolui SK (2021) Blending of cyclic carbonate based on soybean oil and glycerol: a non-isocyanate approach towards the synthesis of polyurethane with high performance. J Polym Res 28:146
Oprea S, Potolinca VO, Oprea V (2018) Influence of the hydroquinone ether moieties and Bisphenol A glycerolate diacrylate on the UV stability behavior of new polyurethane materials. J Polym Res 25:79
Parcheta P, Glowinska E, Datta J (2020) Effect of bio-based components on the chemical structure, thermal stability and mechanical properties of green thermoplastic polyurethane elastomers. Eur Polym J 123:109422
Zhang T, Xie F, Motuzas J, Bryant P, Kurusingal V, Colwell JM, Laycock B (2018) Early-stage photodegradation of aromatic poly(urethane-urea) elastomers. Polym Degrad Stab 157:181–198
Liu L, Wu Y, Zhu Z (2017) Internal structure and crystallinity investigation of segmented thermoplastic polyurethane elastomer degradation in supercritical methanol. Polym Degrad Stab 140:17–24
Kojio K, Nozaki S, Takahara A, Yamasak S (2020) Influence of chemical structure of hard segments on physical properties of polyurethane elastomers: a review. J Polym Res 27:140
Oprea S (2010) Dependence of fungal biodegradation of PEG/castor oil-based polyurethane elastomers on the hard-segment structure. Polym Degrad Stab 95:2396–2404
Oprea S, Timpu D, Oprea V (2019) Design-properties relationships of polyurethanes elastomers depending on different chain extenders structures. J Polym Res 26:117
Clemitson IR (2015) Castable polyurethane elastomers, 2nd Edition Published, by CRC Press ISBN 9781138809208
Wang H, Liu Y, Sun B, Huang S, Tian J (2013) Aging behavior of the polyether polyurethane films irradiated by UV. Adv Mater Res 748:16–21
Govorcin Bajsic E, Zdraveva E (2018) Photooxidative stability of polyurethane/ polycarbonate blends. Chem Biochem Eng Q 32:191–203
Oprea S, Oprea V (2002) Mechanical behavior during different weathering tests of the polyurethane elastomers films. Eur Polym J 38:1205–1211
Zia KM, Bhatti IA, Barikani M, Zuber M (2008) Surface characteristics of UV-irradiated polyurethane elastomers extended with α, ω-alkane diols. Appl Surf Sci 254:6754–6761
Xie F, Zhang T, Bryant P, Kurusingal V, Colwell JM, Laycock B (2019) Degradation and stabilization of polyurethane elastomers. Prog Polym Sci 90:211–268
Zhong Y, You G, Cai S, Yang B (2019) QUV accelerated aging effects on the structure and properties of polyether polyurethane fibers. IOP Conf Series: Mater Sci Eng 562:012043
Toshchevikov VP, Saphiannikova M, Heinrich G (2012) Theory of light-induced deformation of azobenzene elastomers: Influence of network structure. J Chem Phys 137:024903
Saphiannikova M, Toshchevikov V, Ilnytskyi J (2010) Photoinduced deformations in azobenzene polymer films. Nonlinear Opt Quantum Opt 41:27–57
Siampiringue N, Guyot G, Monti S, Bortolus P (1987) The cis-trans photoisomerization of azobenzene: An experimental re-examination. J Photochem 37:185–188
Morishima Y, Tsuji M, Kamaehi M, Hatada K (1992) Photochromic isomerization of azobenzene moieties compartmentalized in hydrophobic microdomains in a microphase structure of amphiphilic polyelectrolytes. Macromolecules 25:4406–4410
Iqbal D, Samiullah MH (2013) Photo-responsive shape-memory and shape-changing liquid-crystal polymer networks. Materials 6:116–142
Kondo M, Sugimoto M, Yamada M, Naka Y, Mamiya J-i, Kinoshita M, Shishido A, Yu Y, Ikeda T (2010) Effect of concentration of photoactive chromophores on photomechanical properties of crosslinked azobenzene liquid- crystalline polymers. J Mater Chem 20:117–122
Van Hoorick J, Ottevaere H, Thienpont H, Dubruel P, Van Vlierberghe S Editors (2018) Polymer and photonic materials towards biomedical breakthroughs. Springer International Publishing AG Switzerland
Wu Y, Natansohn A, Rochon P (2004) Photoinduced birefringence and surface relief gratings in polyurethane elastomers with azobenzene chromophore in the hard segment. Macromolecules 37:6090–6095
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 51:2727–2738
Muzdalo A, Saalfrank P, Vreede J, Santer M (2018) Cis-to-trans isomerization of azobenzene derivatives studied with transition path sampling and quantum mechanical/molecular mechanical molecular dynamics. J Chem Theory Comput 14:2042–2051
Karukatis KK, Perelman LA, Wong WK (2002) Spectroscopic characterization of azo dye aggregation on dendrimer surfaces. Langmuir 18:10363–10371
El-R K, Al-Deyab SS, El-Newehy MH (2010) Controlled release of 5- aminosalicylic acid (5-ASA) from new biodegradable polyurethanes. Molecules 15:2257–2268
Duarah R, Deka A, Karak N (2020) Multifaceted bioinspired hyperbranched polyurethane nanocomposite as a non-contact triggered self-healing material. eXPRESS Polym Lett 14:542–555
Mahkam M, Assadi MG, Zahedifar R, Allahverdipoor M, Doostie L, Djozan J (2004) Synthesis and evaluation of new linear azo-polymers for colonic targeting. Des Monomers Polym 7:351–359
Zemskov AV, Rodionova GN, Tuchin YG, Karpov VV (1988) IR spectra and structure of some azo dyes — p-azobenzene derivatives — In various aggregate states. J Appl Spectrosc 49:1020–1024
Nguyen TL, Saleh MA (2020) Thermal degradation of azobenzene dyes. Results Chem 2:100085
Akram N, Saleem S, Mahmood Zia K, Saeed M, Usman M, Maqsood S, Mumtaz N, Khan WG (2021) Stoichiometric-architectural impact on thermo-mechanical and morphological behavior of segmented polyurethane elastomers. J Polym Res 28:238
Petrovic ZS, Milic J, Zhang F, Ilavsky J (2017) Fast-responding bio-based shape memory thermoplastic polyurethanes. Polymer 121:26–37
Zhu R, Wang Y, Zhang Z, Ma D, Wang X (2016) Synthesis of polycarbonate urethane elastomers and effects of the chemical structures on their thermal, mechanical and biocompatibility properties. Heliyon 2:00125
Premakumari J, Gnana Roy GA, Muthu Prabhu AA, Venkatesh G, Subramanian VK, Rajendiran N (2011) Effect of solvents and pH on β-cyclodextrin inclusion complexation of 2,4-dihydroxyazobenzene and 4-hydroxyazobenzene. J Solution Chem 40:327–347
Funding
This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Competing Interest
The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Oprea, S., Potolinca, V.O. Behavior to UV irradiation of the polyurethanes containing azobenzene side groups in the main chains structure. J Polym Res 28, 369 (2021). https://doi.org/10.1007/s10965-021-02708-6
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s10965-021-02708-6