Abstract
In order to cure hydroxyl-terminated polybutadiene (HTPB) at room temperature, Trimethylisophthtalodinitrile oxide (TINO) was synthesized in four steps from mesitylene with total yield of 42.0%. Its structure was characterized by FT-IR 1H NMR and 13C NMR. Make curing agent TINO/HTPB equals 12, 14, 16, 18 and 20% to prepare the dumbbell-shaped cross-linked polymers. The FT-IR, tensile strength, DSC, TG and contact angle of the cross-linked polymers were tested and analyzed. With the increasing of TINO, tensile strength of cross-linked polymers increased from 0.077 to 0.300 MPa and the elongation at break decreased from about 437 to 104%. The Tg of the crosslink polymers are −75.01, −73.92, −73.42, −70.09 and −71.78 °C, respectively. The contact angles are 116.91°, 100.66°, 93.68°, 86.25° and 87.35°. The results showed that TINO can cure HTPB under room temperature and the cross-linked polymers are expected to be used in the composite solid propellant.
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References
N. Ahmad, M.B. Khan, X.Y. Ma, N. Ul-Haq, The influence of cross-linking/chain extension structures on mechanical properties of htpb-based polyurethane elastomers. Arab. J. Sci. Eng. 39, 43–51 (2014)
Shu Yuan-jie, Huo Ji-chuan, Introduction of Explosive (Chemical Industry Press, Beijing, China, 2011)
K. Hailu, G. Guthausen, W. Becker, A. Konig, A. Bendfeld, E. Geissler, In-situ characterization of the cure reaction of HTPB and IPDI by simultaneous NMR and IR measurements. Polym. Test. 29, 513–519 (2010)
M. Kohga, Application of polytetrahydrofuran as a plasticizer of HTPB binder. Sci. Technol. Energ. Mater. 71, 77–82 (2010)
S.K. Rath, U.G. Suryavansi, M. Patri, Polyurethane sealant based on hydroxy terminated polybutadiene (HTPB) capped with isophorone di-isocyanate (IPDI). J. Polym. Mater. 25, 85–92 (2008)
L.D. Villar, T. Cicaglioni, M.F. Diniz et al., Thermal aging of HTPB/IPDI-based polyurethane as a function of NCO/OHRatio. Mater. Res-Ibero-Am. J. 14, 372–375 (2011)
N. Zheng, S.Y. Jie, B.G. Li, Synthesis, chemical modifications and applications of hydroxyl-terminated polybutadiene. Prog. Chem. 28, 665–672 (2016)
D.H. Lee, K.T. Kim, Y. Jang et al., 1,2,3-Triazole cross-linked polymers as binders for solid rocket propellants. J. Appl. Polym. Sci. 131, 40594 (2014)
T. Keicher, W. Kuglstatter, S. Eisele et al., Isocyanate-free curing of glycidyl azide polymer (GAP) with bis-propargyl-succinate (II). Propell. Explos. Pyrot. 34, 210–217 (2009)
K. Menke, T. Heintz, W. Schweikert et al., Formulation and properties of ADN/GAP propellants. Propell. Explos. Pyrot. 34, 218–230 (2009)
H. Li, F.Q. Zhao, Q.Q. Yu et al., A comparison of triazole cross-linked polymers based on poly-AMMO and GAP: mechanical properties and curing kinetics. J. Appl. Polym. Sci. 133, 43341 (2016)
L. Yudina, C. Eldsäter, P. Goede, et al., Synthesis, analysis and evaluation of 2,4,6-trimethylisophthtalodinitrile-N-oxide as a potential new curing agent for AND-based formulations//International Annual Conference of ICT (2005), 36th (Energetic Materials): 123/1-123/9
B.S. Huffman, R.A. Schultz, P.J. Schlom, Novel reagents for heat-activated polymer crosslinking. Polym. Bull. 47, 159–166 (2001)
S.A. Kotel’nikov, V.S. Sukhinin, A.S. Eemilov, Kinetics of formation and curing of oligoether urethane allyl ester. Russ. J. Appl. Chem. 75, 477–479 (2002)
D.V. Tsyganov, A.P. Yakubov, L.I. Belenkii, et al., Synthesis and properties of stable aromatic bis(nitrile oxides). Russ. Chem. B+ 40, 1238–1243 (1991)
H. Feuer, Nitrile oxides, nitrones, and nitronates in organic synthesis (Wiley, Hoboken, 2008)
E. Hess, J. W. Mcfarland, U.S. Patent 3,258,397 (1966)
X.C. Wang, Y.J. Shu, X.M. Lu et al., Application of 1,3-dipolar cycloaddition reaction in curing energetic binders. Propell. Polym. Mater. 15, 32–37 (2017)
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This work is supported by the National Natural Science Foundation of China (51373159).
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Wang, X. et al. (2018). Trimethylisophthtalodinitrile Oxide as a Room-Temperature Curing Agent for Curing HTPB. In: Han, Y. (eds) Advanced Functional Materials. CMC 2017. Springer, Singapore. https://doi.org/10.1007/978-981-13-0110-0_95
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DOI: https://doi.org/10.1007/978-981-13-0110-0_95
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