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Synthesis and properties of double methyl oleate terminated polysiloxane

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Abstract

Double methyl oleate (MO) capping agent (MO-MM-MO) was prepared by hydrosilylation, from MO and tetramethyldisiloxane (HMMH). The structure was characterized by IR spectrum. By investigating the effects of different catalysts and reaction conditions on the hydrosilylation conversion, the H2PtCl6·6H2O/isopropanol solutions was selected as catalyst, and the optimal reaction conditions were determined. The double MO-terminated polysiloxane (MOM-Dn-MMO) with different degree of polymerization (DP) was prepared via octamethylcyclotetrasiloxane (D4) ring opening polymerization, with MO-MM-MO terminated. The effects of DP on the performance of MOM-Dn-MMO were studied. With the increase in DP, the viscosity–temperature performance of product gradually increases, and it remained basically unchanged, when the DP was 60 or more. For the lubrication performance, as the DP increased, the product lubrication performance improved gradually, and compared with polydimethylsiloxane (M-Dn-M), the lubrication performance of MOM-Dn-MMO was also more excellent. The products with large DP had good thermal stability, also. In addition, the effects of product on the mineral oil performance were also investigated. The MOM-D40-MMO was good compatible with mineral oil, and the lubrication performance of mineral oil with MOM-D40-MMO was also improved, due to the presence of MO.

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Abbreviations

M-Dn-M:

Polydimethylsiloxane

MO:

Methyl oleate

MO-MM-MO:

Double methyl oleate capping agent

HMMH:

Tetramethyldisiloxane

MOM-Dn-MMO:

Double methyl oleate terminated polysiloxane

D4 :

Octamethylcyclotetrasiloxane

DP:

Degree of polymerization

VI:

Viscosity index

VTC:

Viscosity–temperature coefficient

WSD:

Wear scar diameter

TGA:

Thermal gravimetric analyzer

IR:

Infrared

ST:

Surface tension

References

  1. Marciniec B (1992) Comprehensive handbook on hydrosilylation. Pergamon, Oxford. ISBN 9780080402727

    Google Scholar 

  2. Voorhoeve RJH (1967) Organohalosilanes: precursors to silicones. Elsevier, New York

    Google Scholar 

  3. Xing S, Wang Y (2000) Silicone synthesis process and product application. Chemical Industry Press, Beijing. ISBN 9787502528584

    Google Scholar 

  4. Hu S, Sang S, Fu D et al (2012) Synthesis and applications of diphenyl-dimethylsiloxane copolymers. Silicone Mater 26:117–121. https://doi.org/10.3969/j.issn.1009-4369.2012.02.012

    Article  Google Scholar 

  5. Wu C, Jin J, Jiang J et al (2007) Preparation of methyldiphenyl-terminated silicone oil and study on its thermal stabilities. Silicone Mater 21:258–262. https://doi.org/10.3969/j.issn.1009-4369.2007.05.003

    Article  CAS  Google Scholar 

  6. Chung D, Lim JC (2009) Study on the Effect of structure of polydimethylsiloxane grafted with polyethyleneoxide on surface activities. J C Colloid Surf A 336:35–40. https://doi.org/10.1016/j.colsurfa.2008.11.020

    Article  CAS  Google Scholar 

  7. Ji C, Li F, Yun Z (2018) Synthesis and properties of phenyl carboxyl polydimethylsiloxane for fabrics treatment. J Appl Polym Sci 135:45866. https://doi.org/10.1002/app.45866

    Article  CAS  Google Scholar 

  8. Bauer J, Husing N, Kickelbick G (2002) Preparation of functionalized block copolymers based on a polysiloxane backbone by anionic ring-opening polymerization. J Polym Sci Pol Chem 40:1539–1551. https://doi.org/10.1002/pola.10235

    Article  CAS  Google Scholar 

  9. Zhang AQ, Yang L, Lin YL et al (2013) Self-healing supramolecular elastomers based on the multi-hydrogen bonding of low-molecular polydimethylsiloxanes: synthesis and characterization. J Appl Polym Sci 129:2435–2442. https://doi.org/10.1002/app.38832

    Article  CAS  Google Scholar 

  10. Xu YJ, Yin H, Yuan SF et al (2009) Film morphology and orientation of amino silicone adsorbed onto cellulose substrate. Appl Surf Sci 255:8435–8442. https://doi.org/10.1016/j.apsusc.2009.05.149

    Article  CAS  Google Scholar 

  11. Reddy N, Salam A, Yang Y (2008) Effect of structures and concentrations of softeners on the performance properties and durability to laundering of cotton fabrics. Ind Eng Chem Rese 47:2502–2510. https://doi.org/10.1021/ie071564f

    Article  CAS  Google Scholar 

  12. Wyman JE, Rangwalla I (1991) U.S. Patent 5215822

  13. Eckberg RP (1982) U.S. Patent 4348454

  14. Herbert B, Guenter E, Wolfram B (1990) U.S. Patent 4931062

  15. Chu GJ, Wang F, Zhang XJ et al (2014) Effect of sulfurous extreme pressure antiwear agent on tribological properties of phenyl silicone oil. Silicone Mater 28:367–369

    Google Scholar 

  16. Feng X (2011) Tribological properties of fluorosilicone containing oils as lubricant additives. Tribology 31:205–209

    CAS  Google Scholar 

  17. An QF, Fu YS, Hao LF et al (2013) Fabrication of superhydrophobic fabric coating using microphase-separated dodecafluoroheptyl-containing polyacrylate and nanosilica. J Appl Polym Sci 128:3050–3056. https://doi.org/10.1002/app.38503

    Article  CAS  Google Scholar 

  18. An QF, Jia Y, Wang KF (2011) Film morphology, orientation and performance of dodecyl/carboxyl functional polysiloxane on cotton substrates. Appl Surf Sci 257:4569–4574. https://doi.org/10.3321/j.issn:0253-4320.2009.10.011

    Article  CAS  Google Scholar 

  19. Wang CC, Ekstrom L, Lausman T C (1982) U.S. Patent 4342659

  20. Danner B (2010) U.S. Patent 7652120

  21. Teramoto M, Suzuki T, Fujiwara A, et al (2005) J.P. Patent 206955

  22. Li F, Ji C, Yun Z (2018) Synthesis of alkyl polymethylsiloxane (APMS) by condensation reaction and study of properties as lubricants. J Macromol Sci A 55:332–339. https://doi.org/10.1080/10601325.2018.1426388

    Article  CAS  Google Scholar 

  23. Akverts H, Kussi S, Grape W (1987) U.S. Patent 4652386

  24. Quaal QJ, Groenh ED, Kelly RJ (1973) U.S. Patent 3756052

  25. Lin F, Song MZ, He ZZ (2008) Synthesis and structural characterization of methacrylic acid/octadecyl acrylate-graft-poly(methylhydrosiloxane) by hydrosilylation. J Appl Polym Sci 107:3773–3780. https://doi.org/10.1002/app.27487

    Article  CAS  Google Scholar 

  26. Huang W (2013) Silicone release agent. Silicone Mater 27:467–470

    CAS  Google Scholar 

  27. Chu GJ (2013) Study on preparation and properties of lubricating grease with alkyl modified silicone. Silicone Mater 27:15–19

    Google Scholar 

  28. Huang W (2004) Silicon oil and secondary processed products. Chemical Industry Press, Beijing. ISBN 9787502548827

    Google Scholar 

  29. Lin Y, Yan BZ (2004) Synthesis of alkyl siloxane. J B U Chem Tech 31:82–85

    CAS  Google Scholar 

  30. Zhu HJ, Liao HL, Li FY (2006) Synthesis and application of long-chain α-olefins in silicone products. New Chem Mater 34:26–28. https://doi.org/10.3321/j.issn:1003-5214.2005.z1.022

    Article  CAS  Google Scholar 

  31. Guo FG, Li XR (2006) Preparation and application of aminosilicone as a paper softener. China Tran Pulp 21:35–38. https://doi.org/10.3321/j.issn:1000-6842.2006.01.009

    Article  CAS  Google Scholar 

  32. Balic R, Barrere M, Capitao SS (2002) Synthesis of monodisperse poly(dimethylsiloxane) micra- and macroemulsion. Langmuir 18:941–944

    Article  CAS  Google Scholar 

  33. An QF, Cheng GW, Li LS (2006) Synthesis, characterization, and film morphology of dodecylpolysiloxane. J Appl Polym Sci 101:4480–4486. https://doi.org/10.1002/app.24288

    Article  CAS  Google Scholar 

  34. Zhang JY, Kang XL (2011) Preparation of silicone wax by hydrosilylation. Leath Chem 28:5–9

    Google Scholar 

  35. Zhao Q, Li WB, Yao C (2008) Synthesis and lubricant properties of dodecylpolysiloxane. J Nanjing Tech U 30:81–84

    CAS  Google Scholar 

  36. Thami T, Nasr G, Bestal H et al (2008) Functionalization of surface-grafted polymethylhydrosiloxane thin films with alkyl side chains. J Polym Sci Pol Chem 46:3546–3562. https://doi.org/10.1002/pola.22691

    Article  CAS  Google Scholar 

  37. Yang XF, Yan HL, Yao C (2007) Synthesis and properties of poly(methylsiloxane) modified by methyl acrylate. J Nanjing Normal Univ 30:54–57. https://doi.org/10.3969/j.issn.1001-4616.2007.02.012

    Article  CAS  Google Scholar 

  38. Sun XY, Zhu F, Qu YJ (2015) Research of using the modified vegetable oils as biodegradable lubricating base oil. Lubr Oil 30:1–6. https://doi.org/10.3969/j.issn.1002-3119.2015.02.001

    Article  Google Scholar 

  39. Li BQ (2012) Preparation of fatty acid methyl esters. J Huaihai Inst Tech 21:47–50

    CAS  Google Scholar 

  40. Wang ZP, Yu ST (2012) Research on synthesis of methyl oleate catalyzed by acid and base catalysts. Fine Petrochem 13:49–53. https://doi.org/10.3969/j.issn.1009-8348.2012.02.012

    Article  Google Scholar 

  41. Bai YG, Fu LL, Jiang DG (2014) Reaction kinetics of methyl oleate synthesis. J Chem Eng 42:56–60. https://doi.org/10.3969/j.issn.1005-9954.2014.05.014

    Article  CAS  Google Scholar 

  42. Zhou XY, Kang BA, Wu HP et al (2011) Study on the synthesis technology for epoxy methyl oleate. Appl Chem Ind 40:303–306

    CAS  Google Scholar 

  43. Wu GD, Song XQ, Wang P (2008) Study on the synthesis technology for epoxy soybean oil. PLA Addict 5:35–38

    Google Scholar 

  44. Yu L, Nie Y, Chen W (2013) Kinetics of epoxidation and oxirane cleavage of fatty acid methyl ester in formic acid auto catalytic system. Chem Ind Times 27:11–16. https://doi.org/10.3969/j.issn.1002-154X.2013.03.004

    Article  CAS  Google Scholar 

  45. Hang XM, Hua CC (1997) The mechanism and kinetics of oxirane ring cleavage in epoxidized oil with formic acid. J Shanghai Jiaotong Univ 30:40–46

    Google Scholar 

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Correspondence to Zhi Yun.

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Ji, C., Chen, X., Li, F. et al. Synthesis and properties of double methyl oleate terminated polysiloxane. Polym. Bull. 76, 1807–1824 (2019). https://doi.org/10.1007/s00289-018-2473-0

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  • DOI: https://doi.org/10.1007/s00289-018-2473-0

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