Abstract
New high refractive index monomer of 2,5-bis(methylallyl thioester)-thiadiazole (BMATETDZ) containing thioester and dithiazole was synthesized by a one-step condensation reaction with methyl acryloyl chloride and 2,5-dimercaptothiadiazole (DTD). N–N=(C), C=O, and C–S with high molar refraction groups were introduced into the structure of BMATETDZ. FTIR and 1H NMR were used to characterize the molecular structure of BMATETDZ. The refractive index of BMATETDZ was 1.661. The coatings of poly (2,5-bis(methylallyl thioester)-thiadiazole) (C-PBMATETDZ) on polyethylene terephthalate (PET) film were prepared by photopolymerization under UV irradiation. The C-PBMATETDZ coatings exhibited better comprehensive properties with high refractive index, high hardness, good adhesive force, excellent thermal stability, and high transparency in range of 200–900 nm.
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References
You, NH, Higashihara, T, Oishi, Y, Ando, S, Ueda, M, “Highly Refractive Poly (phenylene thioether) Containing Triazine Unit.” Macromolecules, 43 (10) 4613–4615 (2010)
Huang, JC, Chu, YP, Wei, M, Deanin, RD, “Comparison of Epoxy Resins for Applications in Light Emitting Diodes.” Adv. Polym. Technol., 23 (4) 298–306 (2004)
Pagliaro, M, Ciriminna, R, “New Fluorinated Functional Materials.” J. Mater. Chem., 15 (47) 4981–4991 (2005)
Higashihara, T, Ueda, M, “Recent Progress in High Refractive Index Polymers.” Macromolecules, 48 (7) 1915–1929 (2015)
Tojo, Y, Arakwa, Y, Watanabe, J, Konishi, G, “Synthesis of High Refractive Index and Low-birefringence Acrylate Polymers with a Tetraphenylethane Skeleton in the Side Chain.” Polym. Chem., 4 (13) 3807–3812 (2013)
Minns, RA, Gaudiana, RA, “Design and Synthesis of High Refractive Index Polymers. II.” J. Macromol. Sci. A Pure. Appl. Chem., 29 (1) 19–30 (1992)
Paquet, C, Cyr, PW, Kumacheva, E, Manners, I, “Polyferrocenes: Metallopolymers with Tunable and High Refractive Indices.” Chem. Commun., 10 (2) 234–235 (2004)
Liu, J, Ueda, M, Ogura, T, Shibasaki, Y, Ando, S, “Optically Transparent Sulfur-Containing Polyimide-TiO2 Nanocomposite Films with High Refractive Index and Negative Pattern Formatio from Poly(amic acid)−TiO2 Nanocomposite Film.” Chem. Mater., 20 (1) 273–281 (2010)
Chau, JLH, Tung, CT, Lin, YM, Li, AK, “Preparation and Optical Properties of Titania/epoxy Nanocomposite Coatings.” Mater. Lett., 62 (19) 3416–3418 (2008)
Shobha, HK, Johnson, H, Sankarapandian, M, Kim, YS, Rangarajan, P, Baird, DG, McGrath, JE, “Synthesis of High Refractive-Index Melt-stable Aromatic Polyphosphonates.” J. Polym Sci. A Polym. Chem., 39 (39) 2904–2910 (2001)
Ammar, S, Ramesh, K, Vengadaesvaran, B, Ramesh, S, Arof, AK, “Formulation and Characterization of Hybrid Polymeric/ZnO Nanocomposite Coatings with Remarkable Anti-corrosion and Hydrophobic Characteristics.” J. Coat. Technol. Res., 13 (5) 1–10 (2016)
Li, C, Li, Z, Liu, JG, Zhao, XJ, Yang, HX, “Synthesis and Characterization of Organo-Soluble Thioether-Bridged Polyphenylquinoxalines with Ultrahigh Refractive Indices and Low Birefringences.” Polymer, 51 (17) 3851–3858 (2010)
Kim, JS, Cho, BS, Kweon, JO, Noh, ST, “Preparation and Properties of UV-curable Di-functional Sulfur-Containing Thioacrylate and Thiourethane Acrylate Monomers with High Refractive Indices.” Prog. Org. Coat., 77 (11) 1695–1700 (2014)
Matsuda, T, Funke, Y, Yoshida, M, Yamamoto, T, Takara, T, “Optical Material of High Refractive Index Resin Composed of Sulfur-Containing Aromatic Methacrylates.” J. Appl. Polym. Sci., 76 (1) 50–54 (2000)
Kisohen, KB, Chemical Handbook Basic II, p. 520. Chemical Society of Japan, Tokyo, 1986
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The author would like to acknowledge Technology Department of Anhui Province (1301021004), Analysis and Test Center at Hefei University of Technology.
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Zhou, S., Mao, Y., Zhou, Z. et al. Preparation of 2,5-bis(methylallyl thioester)-thiadiazole with high refractive index and its coatings. J Coat Technol Res 14, 1457–1461 (2017). https://doi.org/10.1007/s11998-017-9959-9
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DOI: https://doi.org/10.1007/s11998-017-9959-9