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9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide-based oligosiloxane as a promising damping additive for methyl vinyl silicone rubber (VMQ)

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Abstract

For the first time, we report the damping effect of a novel 9, 10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide (DOPO)-based oligosiloxane abbreviated as DOPO-PMVS on methyl vinyl silicone rubber (VMQ) elastomers. Designed DOPO-PMVS was synthesized by means of hydrophosphination reaction and studied by FT-IR, 1H NMR, 29Si NMR, 31P NMR, and thermogravimetric analysis. The effect of added DOPO-PMVS on damping, mechanical, and thermal properties of VMQ elastomers before and after post-cure was then examined. Interestingly, the dynamic mechanical analysis data showed that the incorporation of 10 wt% DOPO-PMVS significantly improved the damping properties of VMQ elastomers from −20.5 to 200 °C. The effect mechanism was attributed to the hydrogen bonding interactions exerted between DOPO-PMVS and silica. The break and recombination of hydrogen bonding caused by external force resulted in more dissipated energy and enhanced damping properties. Furthermore, the mechanical and thermal properties of VMQ/DOPO-PMVS elastomers were very practical for the application of damping silicon rubber.

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References

  1. Chung DDL (2001) Materials for vibration damping. J Mater Sci 36:5733–5737. doi:10.1023/A:1012999616049

    Article  Google Scholar 

  2. Kwak GH, Inoue K, Tominaga Y, Asai S, Sumita M (2001) Characterization of the vibrational damping loss factor and viscoelastic properties of ethylene-propylene rubbers reinforced with micro-scale fillers. J Appl Polym Sci 82:3058–3066

    Article  Google Scholar 

  3. Fan RP, Meng G, Yang J, He CC (2009) Experimental study of the effect of viscoelastic damping materials on noise and vibration reduction within railway vehicles. J Sound Vib 319:58–76

    Article  Google Scholar 

  4. Xu ZD, Liao YX, Ge T, Xu C (2016) Experimental and theoretical study of viscoelastic dampers with different matrix rubbers. J Eng Mech. doi:10.1061/(ASCE)EM.1943-7889.0001101

  5. Urayama K, Miki T, Takigawa T, Kobjiya S (2004) Damping elastomer based on model irregular networks of end-linked poly(dimethylsiloxane). Chem Mater 16:173–178

    Article  Google Scholar 

  6. Ward IM, Sweeney J (2004) An introduction to the mechanical properties of solid polymers, 2nd edn. John Wiley & Sons Ltd, Chichester, pp 70–72

    Google Scholar 

  7. Fradkin DG, Foster JN, Sperling LH, Thomas DA (1986) A quantitative-determination of the damping behavior of acrylic-based interpenetrating polymer networks. Rubber Chem Technol 59:255–262

    Article  Google Scholar 

  8. Chang MCO, Thomas DA, Sperling LH (1988) Group contribution analysis of the damping behavior of homopolymers, statistical copolymers, and interpenetrating polymer networks based on acrylic, vinyl, and styrenic mers. J Polym Sci Pol Phys 26:1627–1640

    Article  Google Scholar 

  9. Sirisinha C, Prayoonchatphan N (2001) Study of carbon black distribution in BR/NBR blends based on damping properties: influences of carbon black particle size, filler, and rubber polarity. J Appl Polym Sci 81:3198–3203

    Article  Google Scholar 

  10. Su C, Zhao CB, Xu LH, Zhang C (2015) Effects of chemical structure of phenolic resin on damping properties of acrylate rubber-based blends. J Macromol Sci B 54:177–189

    Article  Google Scholar 

  11. Zhang FS, He GS, Xu KM, Wu H, Guo SY, Zhang CL (2014) Damping mechanism and different modes of molecular motion through the glass transition of chlorinated butyl rubber and petroleum resin blends, J Appl Polym Sci. doi:10.1002/app.40464

  12. Lu X, Li XJ, Tian M (2014) Preparation of high damping elastomer with broad temperature and frequency ranges based on ternary rubber blends. Polym Adv Technol 25:21–28

    Article  Google Scholar 

  13. Shi XY, Bi WN, Zhao SG (2012) DMA analysis of the damping of ethylene-vinyl acetate/acrylonitrile butadiene rubber blends. J Appl Polym Sci 124:2234–2239

    Article  Google Scholar 

  14. Manoj NR, Chandrasekhar L, Patri M, Chakraborty BC, Deb PC (2002) Vibration damping materials based on interpenetrating polymer networks of carboxylated nitrile rubber and poly(methyl methacrylate). Polym Adv Technol 13:644–648

    Article  Google Scholar 

  15. Wang YB, Huang ZX, Zhang LM (2006) Damping properties of silicone rubber/polyacrylate sequential interpenetrating networks. Trans Nonferr Metal Soc China 16:S517–S520

    Article  Google Scholar 

  16. Culin J (2016) Interpenetrating polymer network composites containing polyurethanes designed for vibration damping. Polimery-W 61:159–165

    Article  Google Scholar 

  17. Lv XS, Huang ZX, Shi MX, Fan Y, Gao GB (2016) Self-gradient mechanism, morphology and damping analysis of a thickness continuous gradient epoxy–polyurethane interpenetrating polymer network. Rsc Adv 6:111688–111701

    Article  Google Scholar 

  18. Liu J, Li QS, Zhuo YG, Hong W, Lv WF, Xing GZ (2014) Characterization and preparation of P(U-MMA-An) interpenetrating polymer network damping and absorbing material. J Nanosci Nanotechnol 14:4405–4408

    Article  Google Scholar 

  19. Wang C, Jia JR (2014) Damping and mechanical properties of polyol cross-linked polyurethane/epoxy interpenetrating polymer networks. High Perform Polym 26:240–244

    Article  Google Scholar 

  20. Yu WW, Zhang DZ, Du M, Zheng Q (2013) Role of graded length side chains up to 18 carbons in length on the damping behavior of polyurethane/epoxy interpenetrating polymer networks. Eur Polym J 49:1731–1741

    Article  Google Scholar 

  21. Liu MJ, Song GJ, Yi J, Xu YG (2013) Damping analysis of polyurethane/polyacrylate interpenetrating polymer network composites filled with graphite particles. Polym Compos 34:288–292

    Article  Google Scholar 

  22. Chen SB, Wang QH, Wang TM (2012) Damping, thermal, and mechanical properties of carbon nanotubes modified castor oil-based polyurethane/epoxy interpenetrating polymer network composites. Mater Design 38:47–52

    Article  Google Scholar 

  23. Chen SB, Wang QH, Wang TM, Pei XQ (2011) Preparation, damping and thermal properties of potassium titanate whiskers filled castor oil-based polyurethane/epoxy interpenetrating polymer network composites. Mater Design 32:803–807

    Article  Google Scholar 

  24. Chen SB, Wang TM, Wang QH, Pei XQ (2011) Damping properties of polyurethane/epoxy graft interpenetrating polymer network composites filled with short carbon fiber and nano-SiO2. J Macromol Sci B 50:931–941

    Article  Google Scholar 

  25. Mok MM, Kim J, Torkelson JM (2008) Gradient copolymers with broad glass transition temperature regions: design of purely interphase compositions for damping applications. J Polym Sci Pol Phys 46:48–58

    Article  Google Scholar 

  26. Li FK, Larock RC (2002) New soybean oil-styrene-divinylbenzene thermosetting copolymers—IV. Good damping properties. Polym Adv Technol 13:436–449

    Article  Google Scholar 

  27. Leng XF, Wei ZY, Ren YY, Bian YF, Wang QY, Li Y (2016) Copolymerization of L-lactide/trimethylene carbonate by organocatalysis: controlled synthesis of comb-like graft copolymers with side chains with different topologies. Rsc Adv 6:40371–40382

    Article  Google Scholar 

  28. Wang XM, Yin XG, Wang LJ, Zhang C, Gong W, He L (2016) Dynamic mechanical properties, crystallization behaviors, and low-temperature performance of polypropylene random copolymer composites. J Appl Polym Sci. doi:10.1002/app.42960

  29. Perera MCS, Rowen CC (2000) Radiation degradation of MG rubber studied by dynamic mechanical analysis and solid state NMR. Polymer 41:323–334

    Article  Google Scholar 

  30. Koshimura K, Sato H (1992) Application study of styrene-isobutylene-styrene block copolymer as a new thermoplastic elastomer. Polym Bull 29:705–711

    Article  Google Scholar 

  31. Andjelkovic DD, Lu YS, Kessler MR, Larock RC (2009) Novel rubbers from the cationic copolymerization of soybean oils and dicyclopentadiene, 2-mechanical and damping properties. Macromol Mater Eng 294:472–483

    Article  Google Scholar 

  32. Kaneko H, Inoue K, Tominaga Y, Asai S, Sumita M (2002) Damping performance of polymer blend/organic filler hybrid materials with selective compatibility. Mater Lett 52:96–99

    Article  Google Scholar 

  33. Trakulsujaritchok T, Hourston DJ (2006) Damping characteristics and mechanical properties of silica filled PUR/PEMA simultaneous interpenetrating polymer networks. Eur Polym J 42:2968–2976

    Article  Google Scholar 

  34. Remillat C (2007) Damping mechanism of polymers filled with elastic particles. Mech Mater 39:525–537

    Article  Google Scholar 

  35. Ding XB, Zhang HP, Yan X (2009) Effects of small molecular additives on the damping performance of CPE/ZKF/EBP three-component hybrids. J Mater Sci 44:2683–2687. doi:10.1007/s10853-009-3351-9

    Article  Google Scholar 

  36. Varischetti J, Jang JS, Gibson RF, Suhr J (2013) Effect of filler waviness and orientation on the damping behavior of CNF-reinforced epoxy composites. J Mater Sci 48:832–840. doi:10.1007/s10853-012-6803-6

    Article  Google Scholar 

  37. Jiang S, Ji LM (2016) Damping properties and micro-morphology of textile waste rubber powder-AO 2246 composites. J Compos Mater 50:963–970

    Article  Google Scholar 

  38. Lu X, Li XJ (2014) Broad temperature and frequency range damping materials based on epoxidized natural rubber. J Elastom Plast 46:84–95

    Article  Google Scholar 

  39. Ding XB, Liu T, Yan XO (2009) Effect of hydrogen bobnding interactions on the damping properties of the organic hybrids of chlorinated polyethylene and hindered phenol. In: Proceedings of 2009 international conference on advanced fibers and polymer materials, Vols 1 and 2. Shanghai, China, pp 458–460

  40. Shi XY, Li Q, Fu GJ, Jia LY (2014) The effects of a polyol on the damping properties of EVM/PLA blends. Polym Test 33:1–6

    Article  Google Scholar 

  41. Yin XT, Liu CY, Lin Y, Guan AG, Wu GZ (2015) Influence of hydrogen bonding interaction on the damping properties of poly(n- butyl methacrylate)/small molecule hybrids. J Appl Polym Sci. doi:10.1002/app.41954

  42. Chandrasekhar V, Azhakar R, Bickley JF, Steiner A (2006) Influence of O–H center dot center dot center dot O=P hydrogen bonding on the supramolecular architectures of phosphorus-based hydrazones: alternate right- and left-handed fused helical chains based on O–H center dot center dot center dot O=P hydrogen bonds in the crystal structure of C6H5P(O)[N(CH3)N=CHC6H4-p-OH](2). Cryst Growth Des 6:910–914

    Article  Google Scholar 

  43. Miller CD, Miller RC, Rogers W (1958) Phosphine oxides. 5. Intramolecular and intermolecular association. J Am Chem Soc 80:1562–1565

    Article  Google Scholar 

  44. Kosolapoff GM, Mccullough JF (1951) Comparison of hydrogen bonding abilities of some organic compounds of phosphorus. J Am Chem Soc 73:5392–5393

    Article  Google Scholar 

  45. Marandi P, Shabari AR, Pourayoubi M, Alviri, V (2014) The double hydrogen bond acceptor capability of phosphoryl oxygen atom in C6H5P(O)[NHC6H4-4-CH3]2. In: Proceeding of the 20th international conference on phosphorus chemistry. Dublin, Ireland

  46. Tsymbal IG, Ryltsev EV, Egorov YP et al (1981) A Comparison of the proton-acceptor capacity in the hydrogen bond of compounds with P=N and P=O groups. Theor Exp Chem 17:34–40

    Article  Google Scholar 

  47. Zhong HF, Wei P, Jiang PK, Wu D, Wang GL (2007) Synthesis and characteristics of a novel silicon-containing flame retardant and its application in poly[2,2-propane-(bisphenol) carbonate]/acrylonitrile butadiene styrene. J Polym Sci Polym Phys 45:1542–1551

    Article  Google Scholar 

  48. Toldy A, Niedermann P, Szebenyi G, Szolnoki B (2016) Mechanical properties of reactively flame retarded cyanate ester/epoxy resin blends and their carbon fibre reinforced composites. Express Polym Lett 10:1016–1025

    Article  Google Scholar 

  49. Hu JH, Shan JY, Zhao JQ, Tong Z (2016) Isothermal curing kinetics of a flame retardant epoxy resin containing DOPO investigated by DSC and rheology. Thermochim Acta 632:56–63

    Article  Google Scholar 

  50. Zhang YC, Xu GL, Liang Y, Yang J, Hu J (2016) Preparation of flame retarded epoxy resins containing DOPO group. Thermochim Acta 643:33–40

    Article  Google Scholar 

  51. Xu WH, Wirasaputra A, Liu SM, Yuan YC, Zhao JQ (2015) Highly effective flame retarded epoxy resin cured by DOPO-based co-curing agent. Polym Degrad Stab 122:44–51

    Article  Google Scholar 

  52. Huang ZZ, Zhang XH, Qi GR (2009) Novel halogen-free flame retardant thermoset from a hybrid hexakis (methoxymethyl) melamine/phosphorus-containing epoxy resin cured with phenol formaldehyde novolac. Express Polym Lett 3:788–796

    Article  Google Scholar 

  53. Vasiljevic J, Jerman I, Jaksa G et al (2015) Functionalization of cellulose fibres with DOPO-polysilsesquioxane flame retardant nanocoating. Cellulose 22:1893–1910

    Article  Google Scholar 

  54. Hirai T, Han LB (2007) Air-induced anti-Markovnikov addition of secondary phosphine oxides and H-phosphinates to alkenes. Org Lett 9:53–55

    Article  Google Scholar 

  55. Xiong YQ, Jiang ZJ, Xie YY, Zhang XY, Xu WJ (2013) Development of a DOPO-containing melamine epoxy hardeners and its thermal and flame-retardant properties of cured products. J Appl Polym Sci 127:4352–4358

    Article  Google Scholar 

  56. Wang XD, Zhang Q (2004) Synthesis, characterization, and cure properties of phosphorus-containing epoxy resins for flame retardance. Eur Polym J 40:385–395

    Article  Google Scholar 

  57. Ren H, Tang SC, Syed JA, Meng XK (2012) A naphthyl-imide-based epoxy resin: cure kinetics and application in carbon fiber reinforced composites. High Perform Polym 24:580–588

    Article  Google Scholar 

  58. Chien A, Maxwell RS, DeTeresa S, Thompson L, Cohenour R, Balazs B (2006) Effects of filler-polymer interactions on cold-crystallization kinetics in crosslinked, silica-filled methyl vinyl silicone rubber/polydiphenylsiloxane copolymer melts. J Polym Sci Polym Phys 44:1898–1906

    Article  Google Scholar 

  59. Dollase T, Spiess HW, Gottlieb M, Yerushalmi-Rozen R (2002) Crystallization of VMQ: the effect of physical and chemical crosslinks. Europhys Lett 60:390–396

    Article  Google Scholar 

  60. Qian LJ, Zhi JG, Tong B, Shi JB, Yang F, Dong YP (2009) Synthesis and characterization of main-chain liquid crystalline copolyesters containing phosphaphenanthrene side-groups. Polymer 50:4813–4820

    Article  Google Scholar 

  61. Harris GI (1963) 1135. A study of hydrogen bonding in poly(diorganosiloxane)-alphaomega-diols. J Chem Soc. doi:10.1039/jr9630005978

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Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (No. 51503211) without which the work presented in this article would not have been possible. Special acknowledgements are given to Prof. Zemin Xie for his enduring help during the study.

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Liu, B., Gao, X., Zhao, Y. et al. 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide-based oligosiloxane as a promising damping additive for methyl vinyl silicone rubber (VMQ). J Mater Sci 52, 8603–8617 (2017). https://doi.org/10.1007/s10853-017-1085-7

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  • DOI: https://doi.org/10.1007/s10853-017-1085-7

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