An ultraviolet light-responsive polyacrylate film with high fatigue resistance
Tóm tắt
Photochromic materials with stable properties during long-term use have a very broad application prospect. Herein, five kinds of spirooxazines (SO1-SO5) with antioxidant properties were successfully synthesized by blending and covalently bonding antioxidants. Then various photochromic polyacrylate laminating adhesives (PA1-PA7) with good fatigue resistance were prepared by incorporating spirooxazines into polyacrylate. Among them, this study used 2, 6 -di-tert-butyl-4-methylphenol (BHT) as the main antioxidant, and tris (2, 4-di-tert-butylphenyl) phosphite (168) as the auxiliary antioxidant. Upon ultraviolet (UV) activation, these PA films possessed superior photochromism and light responsiveness. Importantly, unlike traditional physical blending photochromic polymers, SO2 was successfully covalently bonded into PA through reaction (PA6), effectively improving the fatigue resistance and thermal stability of the PA film. Doping with BHT, it further improved the photochromic properties of the compound film (PA7).
Tài liệu tham khảo
Crano JC, Guglielmetti RJ (2002) [Topics in Applied Chemistry] Organic Photochromic and Thermochromic Compounds || Photochromic Polymers. (Chapter 2):9–63. https://doi.org/10.1007/b115590
He Z, Wang Y, Fang Y, Meng Q (2019) A photocuring PUA material with adjustable flexibility used in the fast photochromic coating on ophthalmic lenses. Prog Org Coat 137. https://doi.org/10.1016/j.porgcoat.2019.105330
Li X, Li J, Wang Y, Matsuura T, Meng J (2004) Synthesis of functionalized spiropyran and spirooxazine derivatives and their photochromic properties. J Photochem Photobiol A 161(2):201–213. https://doi.org/10.1016/S1010-6030(03)00349-6
Yang S, Pang M, Meng J (2011) Progress in Research of Bifunctional Spirobenzopyran and Spironaphthooxazine Photochromic Compounds. Chin J Org Chem 31(11):1725–1735. https://doi.org/10.1055/s-0030-1260234
Minkin VI (2004) Photo-, Thermo-, Solvato-, and Electrochromic Spiroheterocyclic Compounds. ChemInform 35(32):2751–2776. https://doi.org/10.1002/chin.200432274
Schneider S, Mindl A, And GE, Melzig M (1987) Photochromism of spirooxazines I. Investigation of the primary processes in the ring-opening reaction by picosecond time-resolved absorption and emission spectroscopy. Berichte der Bunsengesellschaft für physikalische Chemie. https://doi.org/10.1002/bbpc.19870911126
Ivashenko O, Herpt J, Feringa BL, Rudolf P, Browne WR (2013) UV/Vis and NIR Light-Responsive Spiropyran Self-Assembled Monolayers. Langmuir 29(13):4290–4297. https://doi.org/10.1021/la400192c
Keyvan J, Mahdavian AR, Khoei S, Esfahani AJ (2016) FRET-based acrylic nanoparticles with dual-color photoswitchable properties in DU145 human prostate cancer cell line labeling. Polymer 98:263–269. https://doi.org/10.1016/j.polymer.2016.06.042
Natali M, Giordani S (2012) Interaction studies between photochromic spiropyrans and transition metal cations: the curious case of copper. Org Biomol Chem 10(6):p.1162–1171. https://doi.org/10.1039/c1ob06375h
Baillet G, Campredon M, Guglielmetti R, Giusti G, Aubert C (1994) Dealkylation of N-substituted indolinospironaphthoxazine photochromic compounds under UV irradiation. J Photochem Photobiol A Chem 83(2):147–151. https://doi.org/10.1016/1010-6030(94)03816-3
Baillet G, Giusti G, Guglielmetti R (2006) Study of the Fatigue Process and Yellowing of Polymeric Films Containing Spirooxazine Photochromic Compounds. Bullchemsocjpn 68(4):1220–1225. https://doi.org/10.1246/bcsj.68.1220
Wang JY, Feng CG (2007) Progress on Synthesis of Photochromic Spirooxazines. Chin J Appl Chem
Lampert CM (1987) Advanced optical materials for energy efficiency and solar conversion. Sol Wind Technol 4(3):347–379. https://doi.org/10.1007/978-94-009-3941-7_11
Yuan L, Cai G, Gao J (2019) Synthesis, properties and application in polyvinyl butyral of spirooxazine photochromic compounds. Pigment and Resin Technology, ahead-of-print(ahead-of-print). https://doi.org/10.1108/PRT-12-2018-0125
Guan X, Yan S, Chang J, Yang G, Fan H (2018) Light-induced desorption of trivalent chromium from adsorbents: one step closer to sustainability. Chem Commun 54(90):12770–12773. https://doi.org/10.1039/C8CC08099B
Liu G, Cui C, Jiang L, Gao H, Gao J (2021) Visible light-induced hydrogels towards reversible adsorption and desorption based on trivalent chromium in aqueous solution. React Funct Polym. https://doi.org/10.1016/j.reactfunctpolym.2021.104886
Lei Y, Shi Y, Jiang L, Lei J, Wu B (2020) Photochromism of photopolymerized novel copolymers having spirooxazine moiety groups. Iran Polym J 29(8). https://doi.org/10.1007/s13726-020-00830-8
Gao D, Rui C, Lyu B, Ma J, Duan X (2018) Preparation of epoxy-acrylate copolymer/nano-silica via Pickering emulsion polymerization and its application as printing binder. Appl Surf Sci 435(MAR.30):195–202. https://doi.org/10.1016/j.apsusc.2017.11.063
Sineokov AP, Khamidulova ZS, Aronovich DA, Murokh AF, Knyazev EF (2008) New developments in the field of reactive acrylic adhesives and sealing materials. Polym Sci Ser D 1(2):91–96. https://doi.org/10.1134/S1995421208020044
Chen ZH, Ai-Ting MU, Gao FF (2012) Orthogonal test study on synthesis of alcohol-soluble polyacrylate by semi-bulk polymerization. Electroplating & Finishing
Wen Z, Liu X, Yun Y, Wu S, Cui Y (2017) Preparation of waterborne acrylate laminating adhesive. China Adhesives
Jin ZL (2009) Study of Crosslinkably Modified Alcohol-Soluble Polyacrylate Used for Laminated Adhesive. Chemical Materials for Construction
Dgab D, Mzab D, Blb D, Jmb D, Yun LC (2020) Preparation of amphiphilic Janus SiO2 particles and its application on polyacrylate emulsion - ScienceDirect. Colloids Surf A Physicochem Eng Asp 607. https://doi.org/10.1016/j.colsurfa.2020.125295
Liufu SC, Xiao HN, Li YP (2005) Thermal analysis and degradation mechanism of polyacrylate/ZnO nanocomposites. Polym Degrad Stab 87(1):103–110. https://doi.org/10.1016/j.polymdegradstab.2004.07.011
Li J, Xu H, Shi J, Li C, Bao C (1999) Studies of the major degradation products of a higher alkyl polyacrylate using pyrolysis gas chromatography–mass spectrometry. Anal Chim Acta. https://doi.org/10.1016/S0003-2670(99)00543-7
Saita T (1983) Degradation of Sodium-Polyacrylate in Dilute Aqueous Solution. Jpn J Appl Phys 19(12):2501–2506. https://doi.org/10.1143/JJAP.19.2501
Kim BH, Hwang DG, Kim N, Hong M, Cho SH (2014) Investigation of the thermal degradation of polyacrylate adhesives by evolved gas analysis-(gas chromatography)-mass spectrometry. J Anal Appl Pyrolysis 110:213–319. https://doi.org/10.1016/j.jaap.2014.09.005
Kanwal F, Pethrick RA, Jamil T (2007) Ultrasonic Degradation Studies of Polyacrylates. J Chem Soc Pak 29(5):433–437
Liang D, Du C, Ma F, Shen Y, Wu K (2018) Degradation of Polyacrylate in the Outdoor Agricultural Soil Measured by FTIR-PAS and LIBS. Polymers 10(12):1296. https://doi.org/10.3390/polym10121296
Pongpilaipruet A, Magaraphan R (2015) Synthesis, characterization and degradation behavior of admicelled polyacrylate-natural rubber. Materials Chem Phys 160:194–204. https://doi.org/10.1016/j.matchemphys.2015.04.024
Bugaenko DI, Karchava AV, Yurovskaya MA (2018) Synthesis of Indoles: Recent Advances. Russ Chem Rev 87(2).
Osterby B, Mckelvey RD, Hill L (1991) Photochromic sunglasses: A patent-based advanced organic synthesis project and demonstration. J Chem Educ 68(5):424–425. https://doi.org/10.1021/ed068p424
Kim SH, Shin CJ, Choi MS, Wang S (2008) Self-assembly multilayer of photochromic bolaform spiroxazine. Dyes and Pigments 77(1):70–74. https://doi.org/10.1016/j.dyepig.2007.03.009
Raymo FM, Giordani S (2001) Signal processing at the molecular level. J Am Chem Soc 123(19):4651–4652. https://doi.org/10.1021/ja005699n
Wu L, Zhang S, Qiang P, Lei J, Gao J (2016) Preparation of a spirooxazine grafted PMMA and its photochromic properties. Synth Commun
Kakishita T, Matsumoto K, Kiyotsukuri T, Matsumura K, Hosoda M (1992) Synthesis and NMR study of 9′‐substituted spiroindolinonaphthoxazine derivatives. J Heterocyclic Chem 29(7):1709–1715. https://doi.org/10.1002/jhet.5570290706
Andersson J, Li S, Lincoln P, Andréasson J (2008) Photoswitched DNA-Binding of a Photochromic Spiropyran. J Am Chem Soc 130(36):11836–11837. https://doi.org/10.1021/ja801968f
Bing WU, Cheng-Shi F, Yu-Chuan Z (2007) Synthesis of Side-chain Liquid Crystalline Polyacrylate and Its Liquid Crystalline Property. Chinese Journal of Liquid Crystals and Displays. https://doi.org/10.1007/s12105-007-0028-z
Gushiken T, Saito M, Ubukata T, Yokoyama Y (2010) Fast decoloration of spironaphthooxazine bound to a poly(dimethylsiloxane) network. Photochem Photobiol Sci 9(2):162–171. https://doi.org/10.1039/b9pp00113a
Griffiths J (1976) Colour and constitution of organic molecules. Academic Press