Skip to main content
Top

2018 | OriginalPaper | Chapter

Trimethylisophthtalodinitrile Oxide as a Room-Temperature Curing Agent for Curing HTPB

Authors : Xiaochuan Wang, Yuanjie Shu, Yonglin Lei, Jichuan Huo, Xianming Lu, Qian Zhang, Yingying Lu, Wei Wang

Published in: Advanced Functional Materials

Publisher: Springer Singapore

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

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.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literature
1.
go back to reference 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)CrossRef 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)CrossRef
2.
go back to reference Shu Yuan-jie, Huo Ji-chuan, Introduction of Explosive (Chemical Industry Press, Beijing, China, 2011) Shu Yuan-jie, Huo Ji-chuan, Introduction of Explosive (Chemical Industry Press, Beijing, China, 2011)
3.
go back to reference 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)CrossRef 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)CrossRef
4.
go back to reference M. Kohga, Application of polytetrahydrofuran as a plasticizer of HTPB binder. Sci. Technol. Energ. Mater. 71, 77–82 (2010) M. Kohga, Application of polytetrahydrofuran as a plasticizer of HTPB binder. Sci. Technol. Energ. Mater. 71, 77–82 (2010)
5.
go back to reference 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) 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)
6.
go back to reference 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) 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)
7.
go back to reference N. Zheng, S.Y. Jie, B.G. Li, Synthesis, chemical modifications and applications of hydroxyl-terminated polybutadiene. Prog. Chem. 28, 665–672 (2016) N. Zheng, S.Y. Jie, B.G. Li, Synthesis, chemical modifications and applications of hydroxyl-terminated polybutadiene. Prog. Chem. 28, 665–672 (2016)
8.
go back to reference 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) 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)
9.
go back to reference 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)CrossRef 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)CrossRef
10.
go back to reference K. Menke, T. Heintz, W. Schweikert et al., Formulation and properties of ADN/GAP propellants. Propell. Explos. Pyrot. 34, 218–230 (2009)CrossRef K. Menke, T. Heintz, W. Schweikert et al., Formulation and properties of ADN/GAP propellants. Propell. Explos. Pyrot. 34, 218–230 (2009)CrossRef
11.
go back to reference 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) 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)
12.
go back to reference 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 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
13.
go back to reference B.S. Huffman, R.A. Schultz, P.J. Schlom, Novel reagents for heat-activated polymer crosslinking. Polym. Bull. 47, 159–166 (2001)CrossRef B.S. Huffman, R.A. Schultz, P.J. Schlom, Novel reagents for heat-activated polymer crosslinking. Polym. Bull. 47, 159–166 (2001)CrossRef
14.
go back to reference 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) 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)
15.
go back to reference 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)CrossRef 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)CrossRef
16.
go back to reference H. Feuer, Nitrile oxides, nitrones, and nitronates in organic synthesis (Wiley, Hoboken, 2008) H. Feuer, Nitrile oxides, nitrones, and nitronates in organic synthesis (Wiley, Hoboken, 2008)
17.
go back to reference E. Hess, J. W. Mcfarland, U.S. Patent 3,258,397 (1966) E. Hess, J. W. Mcfarland, U.S. Patent 3,258,397 (1966)
18.
go back to reference 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) 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)
Metadata
Title
Trimethylisophthtalodinitrile Oxide as a Room-Temperature Curing Agent for Curing HTPB
Authors
Xiaochuan Wang
Yuanjie Shu
Yonglin Lei
Jichuan Huo
Xianming Lu
Qian Zhang
Yingying Lu
Wei Wang
Copyright Year
2018
Publisher
Springer Singapore
DOI
https://doi.org/10.1007/978-981-13-0110-0_95

Premium Partners