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Iranian Polymer Journal

, Volume 28, Issue 11, pp 943–955 | Cite as

Synthesis of an alkynyl neutral polymer-bonding agent and its enhancing effect on tensile strength of glycidyl azide polymer-based propellants

  • Shuiping ZhouEmail author
  • Gen Tang
  • Aimin Pang
  • Xiang Guo
  • Fang Wu
  • Huibin Song
  • Xingxing Xu
  • Xiang Hu
  • Yanpin Wang
Original Research
  • 50 Downloads

Abstract

A novel alkynyl neutral polymer-bonding agent (NPBA) was synthesized by a three-step approach. The molecular structure and thermal characteristics of alkynyl NPBA were analyzed. To reveal the influence of alkynyl NPBA on the mechanical properties of glycidyl azide polymer (GAP)-based propellants, two types of GAP propellants with Desmodur N-100 and alkynyl-terminated polyethylene glycol (APE) as curing agents were prepared and mechanical properties of the propellants were fully investigated. Tensile strength and initial modulus of propellants were notably promoted with the increase in alkynyl groups content of alkynyl NPBA with Desmodur N-100 as curing agent. The interfacial adhesion property between GAP binders and CL-20 fillers was greatly improved by alkynyl NPBA, and dewetting phenomenon of propellants during uniaxial tension was markedly attenuated. The wettability of GAP binders and solid fillers was good and the enhancing effect of alkynyl NPBA on tensile strength of GAP propellants was notable. Tensile strength and initial modulus of propellants were notably increased and their maximum elongation was decreased with the increase of alkynyl group content of alkynyl NPBA in propellants when APE was used as a curing agent. In addition, the dynamic mechanical analysis results showed that internal friction resistance of GAP molecular segment motion of GAP propellants was increased and interactions between GAP binder and solid fillers became much stronger with alkynyl NPBA. A notable enhancement effect on tensile strength and initial modulus of GAP propellants was demonstrated with alkynyl NPBA as bonding agent.

Keywords

Alkynyl neutral polymer-bonding agent GAP propellants Alkynyl group Mechanical properties Tensile strength 

Notes

Acknowledgements

The work was supported by the Natural Science Foundation of China (Grant no. 51572075 and 51701067).

Compliance with ethical standards

Conflict of interest

There are no conflicts of interest to declare.

Supplementary material

13726_2019_756_MOESM1_ESM.pdf (365 kb)
Supplementary file1 (PDF 364 kb)

References

  1. 1.
    Guery JF, Chang IS, Shimada T, Glick M, Boury D, Robert E, Napior J, Wardle R (2010) Solid propulsion for space applications: an updated roadmap. Acta Astronaut 66:201–219CrossRefGoogle Scholar
  2. 2.
    Huiru C, Guojin T, Zhibin S (2017) A three-dimensional viscoelastic constitutive model of solid propellant considering viscoelastic Poisson’s ratio and its implementation. Eur J Mech A Solid 61:235–244CrossRefGoogle Scholar
  3. 3.
    Buszek RJ, Soto D, Dailey JM, Bolden S, Tall TL, Hudgens LM, Marshall CA, Boatz JA, Drake GW (2018) Structures and binding energies of nitrate plasticizers DEGDN, TEGDN, and nitroglycerine. Propellants Explos Pyrotech 43:115–121CrossRefGoogle Scholar
  4. 4.
    Davenas A (2003) Development of modern solid propellants. J Propul Power 19:1108–1128CrossRefGoogle Scholar
  5. 5.
    Badgujar DM, Talawar MB, Zarko VE, Mahulikar PP (2017) New directions in the area of modern energetic polymers: an overview. Combust Explos Shock 53:371–387CrossRefGoogle Scholar
  6. 6.
    Deng JK, Wang XQ, Li GP, Luo YJ (2017) Effect of bonding agent on the mechanical properties of GAP high-energy propellant. Propellants Explos Pyrotech 42:394–400CrossRefGoogle Scholar
  7. 7.
    Landsem E, Jensen TL, Hansen FK, Unneberg E, Kristensen TE (2012) Neutral polymeric bonding agents (NPBA) and their use in smokeless composite rocket propellants based on HMX-GAP-BuNENA. Propellants Explos Pyrotech 37:581–591CrossRefGoogle Scholar
  8. 8.
    Pande SM, Sadavarte VS, Bhowmik D (2012) NG plasticized PE-PCP binder-based advanced solid rocket propellants: studies on mechanical properties. Int J Energ Mater Chem Propul 11:123–134Google Scholar
  9. 9.
    Byoung SM (2008) Characterization of the plasticized GAP/PEG and GAP/PCL block copolyurethane binder matrices and its propellants. Propellants Explos Pyrotech 33:131–138CrossRefGoogle Scholar
  10. 10.
    Deng JK, Li GP, Xia M, Lan YF, Luo YJ (2016) Improvement of mechanical characteristics of glycidyl azide polymer binder system by addition of flexible polyether. J Appl Polym Sci 133:43840CrossRefGoogle Scholar
  11. 11.
    Simpson RL, Urtiew PA, Ornellas DL, Moody GL, Scribner KJ, Hoffman DM (1997) CL-20 Performance exceeds that of HMX and its sensitivity is moderate. Propellants Explos Pyrotech 22:249–255CrossRefGoogle Scholar
  12. 12.
    Kim CS, Noble PN, Youn CH, Tarrant D, Gao A (1992) The mechanism of filler reinforcement from addition of neutral polymeric bonding agents to energetic polar propellants. Propellants Explos Pyrotech 17:51–58CrossRefGoogle Scholar
  13. 13.
    Doukkali M, Gauthier E, Patel RB, Stepanov V, Hadim H (2017) Modifying the wettability of nitramine explosives using anionic, cationic and nonionic surfactants. Propellants Explos Pyrotech 42:1185–1190CrossRefGoogle Scholar
  14. 14.
    Holtz EV, Ornellas D, Foltz MF, Clarkson JE (1994) The solubility of ε-cl-20 in selected materials. Propellants Explos Pyrotech 19:206–212CrossRefGoogle Scholar
  15. 15.
    Rao S, Krishna Y, Rao BN (2005) Fracture toughness of nitramine and composite solid propellants. Mater Sci Eng A 403:125–133CrossRefGoogle Scholar
  16. 16.
    Gallier S, Hiernard F (2008) Microstructure of composite propellants using simulated packings and X-Ray Tomography. J Propuls Power 24:147–150CrossRefGoogle Scholar
  17. 17.
    Cho J, Joshi MS, Sun CT (2006) Effect of inclusion size on mechanical properties of polymeric composites with micro and nano particles. Compos Sci Technol 66:1941–1952CrossRefGoogle Scholar
  18. 18.
    Fu SY, Feng XQ, Lauke B, Mai YW (2008) Effects of particle size, particle/matrix interface adhesion and particle loading on mechanical properties of particulate–polymer composites. Compos Part B Eng 39:933–961CrossRefGoogle Scholar
  19. 19.
    Toulemonde PA, Diani J, Gilormini P, Desgardin N, Neviere R (2017) Effects of small particles on the mechanical behavior and on the local damage of highly filled elastomers. J Mater Sci 52:878–888CrossRefGoogle Scholar
  20. 20.
    Bellerby JM, Kiriratnikom C (1989) Explosive-binder adhesion and dewetting in nitramine-filled energetic materials. Propellants Explos Pyrotech 14:82–85CrossRefGoogle Scholar
  21. 21.
    Tan H, Huang Y, Liu C (2008) The viscoelastic composite with interface debonding. Compos Sci Technol 68:3145–3149CrossRefGoogle Scholar
  22. 22.
    Chen JK, Huang ZP, Mai YW (2003) Constitutive relation of particulate-reinforced viscoelastic composite materials with debonded microvoids. Acta Mater 51:3375–3384CrossRefGoogle Scholar
  23. 23.
    Liu YF, Chen Y, Shi L, Yao WS (2012) Synthesis of three novel laurylamine-derived long-chain alkyl bonding agents and their interactions with RDX. Propellants Explos Pyrotech 37:69–76CrossRefGoogle Scholar
  24. 24.
    Zhang ZJ, Luo N, Wang Z, Luo YJ (2015) Polyglycidyl nitrate (PGN)-based energetic thermoplastic polyurethane elastomers with bonding functions. J Appl Polym Sci 132:42026Google Scholar
  25. 25.
    Toulemonde PA, Diani J, Gilormini P, Desgardin N (2016) On the account of a cohesive interface for modeling the behavior until break of highly filled elastomers. Mech Mater 93:124–133CrossRefGoogle Scholar
  26. 26.
    Allen H (1973) Composite solid propellant with additive to improve the mechanical properties thereof. US Patent 3745074Google Scholar
  27. 27.
    Azoug A, Nevière R, Pradeilles-Duval RM, Constantinescu A (2014) Influence of fillers and bonding agents on the viscoelasticity of highly filled elastomers. J Appl Polym Sci 131:40664Google Scholar
  28. 28.
    Oliveira JIS, Pires DC, Diniz MF, Siqueira JL, Mattos EC, Rezende LC, Iha K, Dutra RCL (2014) Determination of primary amine content in bonding agent used in composite solid propellants. Propellants Explos Pyrotech 39:538–544CrossRefGoogle Scholar
  29. 29.
    Hori K, Iwama A, Fukuda T (1990) FTIR spectroscopic study on the interaction between ammonium perchlorate and bonding agents. Propellants Explos Pyrotech 15:99–102CrossRefGoogle Scholar
  30. 30.
    Kim CS, Youn H, Noble PN, Gao A (1992) Developement of neutral polymeric bonding agents for propellants with polar composites filled with organic nitramine crystals. Propellants Explos Pyrotech 17:38–42CrossRefGoogle Scholar
  31. 31.
    Kim CS (1990) Filler reinforcement of polyurethane binder using a neutral polymeric bonding agent. US Patent 4915755Google Scholar
  32. 32.
    Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 40:2004–2021CrossRefGoogle Scholar
  33. 33.
    Katritzky AR, Meher NK, Hanci S, Gyanda R, Tala SR, Mathai S, Duran RS, Bernard S, Sabri F, Singh SK, Ciaramitaro DA (2008) Preparation and characterization of 1, 2, 3-triazole-cured polymers from endcapped azides and alkynes. J Polym Sci Pol Chem 46:238–256CrossRefGoogle Scholar
  34. 34.
    Min BS, Park YC, Ji CY (2012) A study on the triazole crosslinked polymeric binder based on glycidyl azide polymer and dipolarophile curing agents. Propellants Explos Pyrotech 37:59–68CrossRefGoogle Scholar
  35. 35.
    Keicher T, Kuglstatter W, Eisele S, Wetzel T (2009) Isocyanate free curing of glycidyl azide polymer (GAP) with bispropargyl-succinate (II). Propellants Explos Pyrotech 34:210–217CrossRefGoogle Scholar
  36. 36.
    Sonawane S, Anniyappan M, Athar J, Singh A, Talawar MB, Sinha RK, Banerjee S, Sikder AK (2017) Isocyanate-free curing of glycidyl azide polymer with bis-propargylhydroquinone. Propellants Explos Pyrotech 42:386–393CrossRefGoogle Scholar

Copyright information

© Iran Polymer and Petrochemical Institute 2019

Authors and Affiliations

  1. 1.Science and Technology on Aerospace Chemical Power LaboratoryHubei Institute of Aerospace Chemical TechnologyXiangyangChina
  2. 2.Hubei Institute of Aerospace Chemical TechnologyXiangyangChina

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