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

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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.

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References

  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 66:201–219

    Article  CAS  Google Scholar 

  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 61:235–244

    Article  Google Scholar 

  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 43:115–121

    Article  CAS  Google Scholar 

  4. Davenas A (2003) Development of modern solid propellants. J Propul Power 19:1108–1128

    Article  CAS  Google Scholar 

  5. Badgujar DM, Talawar MB, Zarko VE, Mahulikar PP (2017) New directions in the area of modern energetic polymers: an overview. Combust Explos Shock 53:371–387

    Article  Google Scholar 

  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 42:394–400

    Article  CAS  Google Scholar 

  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 37:581–591

    Article  CAS  Google Scholar 

  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 11:123–134

    CAS  Google Scholar 

  9. Byoung SM (2008) Characterization of the plasticized GAP/PEG and GAP/PCL block copolyurethane binder matrices and its propellants. Propellants Explos Pyrotech 33:131–138

    Article  Google Scholar 

  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 133:43840

    Article  Google Scholar 

  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 22:249–255

    Article  CAS  Google Scholar 

  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 17:51–58

    Article  CAS  Google Scholar 

  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 42:1185–1190

    Article  CAS  Google Scholar 

  14. Holtz EV, Ornellas D, Foltz MF, Clarkson JE (1994) The solubility of ε-cl-20 in selected materials. Propellants Explos Pyrotech 19:206–212

    Article  Google Scholar 

  15. Rao S, Krishna Y, Rao BN (2005) Fracture toughness of nitramine and composite solid propellants. Mater Sci Eng A 403:125–133

    Article  Google Scholar 

  16. Gallier S, Hiernard F (2008) Microstructure of composite propellants using simulated packings and X-Ray Tomography. J Propuls Power 24:147–150

    Article  Google Scholar 

  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 66:1941–1952

    Article  CAS  Google Scholar 

  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 39:933–961

    Article  Google Scholar 

  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 52:878–888

    Article  CAS  Google Scholar 

  20. Bellerby JM, Kiriratnikom C (1989) Explosive-binder adhesion and dewetting in nitramine-filled energetic materials. Propellants Explos Pyrotech 14:82–85

    Article  CAS  Google Scholar 

  21. Tan H, Huang Y, Liu C (2008) The viscoelastic composite with interface debonding. Compos Sci Technol 68:3145–3149

    Article  CAS  Google Scholar 

  22. Chen JK, Huang ZP, Mai YW (2003) Constitutive relation of particulate-reinforced viscoelastic composite materials with debonded microvoids. Acta Mater 51:3375–3384

    Article  CAS  Google Scholar 

  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 37:69–76

    Article  Google Scholar 

  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 132:42026

    Google Scholar 

  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 93:124–133

    Article  Google Scholar 

  26. Allen H (1973) Composite solid propellant with additive to improve the mechanical properties thereof. US Patent 3745074

  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 131:40664

    Google Scholar 

  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 39:538–544

    Article  CAS  Google Scholar 

  29. Hori K, Iwama A, Fukuda T (1990) FTIR spectroscopic study on the interaction between ammonium perchlorate and bonding agents. Propellants Explos Pyrotech 15:99–102

    Article  CAS  Google Scholar 

  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 17:38–42

    Article  CAS  Google Scholar 

  31. Kim CS (1990) Filler reinforcement of polyurethane binder using a neutral polymeric bonding agent. US Patent 4915755

  32. Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 40:2004–2021

    Article  CAS  Google Scholar 

  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 46:238–256

    Article  CAS  Google Scholar 

  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 37:59–68

    Article  CAS  Google Scholar 

  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 34:210–217

    Article  CAS  Google Scholar 

  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 42:386–393

    Article  CAS  Google Scholar 

Download references

Acknowledgements

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

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Correspondence to Shuiping Zhou.

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Zhou, S., Tang, G., Pang, A. et al. Synthesis of an alkynyl neutral polymer-bonding agent and its enhancing effect on tensile strength of glycidyl azide polymer-based propellants. Iran Polym J 28, 943–955 (2019). https://doi.org/10.1007/s13726-019-00756-w

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  • DOI: https://doi.org/10.1007/s13726-019-00756-w

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