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Synthesis and thermal characterization of novel poly(tetramethyl-1,3-silphenylenesiloxane) derivative bearing adamantyl moiety

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Abstract

A novel poly(tetramethyl-1,3-silphenylenesiloxane) derivative having adamantyl moiety, i.e., poly(tetramethyl-5-adamantyl-1,3-silphenylenesiloxane) (P1) was synthesized by solution polycondensation of a novel disilanol monomer, i.e., 1-[3,5-(dimethylhydroxysilyl)phenyl]adamantane (M1). M1 was prepared by the Grignard reaction using chlorodimethylsilane and 1-(3,5-dibromophenyl)adamantane, followed by the hydrolysis catalyzed by 5% palladium on charcoal. P1 exhibited the good solubility in common organic solvents, such as tetrahydrofuran (THF), chloroform, dichloromethane, benzene, and toluene at ambient temperature. P1 was also soluble in hot hexane, diethyl ether, and ethyl acetate. The glass transition temperature (T g) and temperature at 5% weight loss (T d5) of P1 were 85 and 517 °C, respectively, and much higher than those of poly(tetramethyl-1,3-silphenylenesiloxane), indicating that P1 is a new polysiloxane derivative with good solubility as well as good thermostability.

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References

  1. Fort RC Jr, Schleyer PR (1964) Adamantane: consequences of the diamondoid structure. Chem Rev 64:277–300

    Article  CAS  Google Scholar 

  2. Malik AA, Archibald TG, Baum K, Unroe MR (1992) Thermally stable polymers based on acetylene-terminated adamantanes. J Polym Sci Part A Polym Chem 30:1747–1754

    Article  CAS  Google Scholar 

  3. Pixton MR, Paul DR (1995) Gas transport properties of adamantane-based polysulfones. Polymer 36:3165–3172

    Article  CAS  Google Scholar 

  4. Chern YT, Chung WH (1996) Preparation and properties of polyamides and polyimides derived from 1,3-diaminoadamantane. J Polym Sci Part A Polym Chem 34:117–124

    Article  CAS  Google Scholar 

  5. Chern YT (1996) Preparation and properties of new polyimides derived from 1,6-diaminodiamantane. J Polym Sci Part A Polym Chem 34:125–131

    Article  CAS  Google Scholar 

  6. Chern YT, Shiue HC (1997) Low dielectric constants of soluble polyimides based on adamantane. Macromolecules 30:4646–4651

    Article  CAS  Google Scholar 

  7. Kameshima H, Nemoto N, Sanda F, Endo T (2002) Cationic ring-opening polymerization of five-membered cyclic thiocarbonate bearing an adamantane moiety via selective ring-opening direction. Macromolecules 35:5769–5773

    Article  CAS  Google Scholar 

  8. Nemoto N, Ito Y, Endo T (2003) Cationic ring-opening polymerization behavior of a five-membered cyclic thiocarbonate having a spiro-linked adamantane moiety. J Polym Sci Part A Polym Chem 41:699–707

    Article  CAS  Google Scholar 

  9. Liaw DJ, Huang CC, Chen WH (2006) Optically transparency and light color of novel highly organosoluble alicyclic polyimides with 4-tert-butylcyclohexyl group. Macromol Chem Phys 207:434–443

    Article  CAS  Google Scholar 

  10. Hattori Y, Miyajima T, Sakai M, Nagase Y, Nemoto N (2008) Synthesis and thermal characterization of novel adamantane-based polysiloxane. Polymer 49:2825–2831

    Article  CAS  Google Scholar 

  11. Matsumoto A, Tanaka S, Otsu T (1991) Synthesis and characterization of poly(1-adamantyl methacrylate): effects of the adamantyl group on radical polymerization kinetics and thermal properties of the polymer. Macromolecules 24:4017–4024

    Article  CAS  Google Scholar 

  12. Chern YT (1996) Radical polymerization and antibacterial activity of copolymers based on N-1-adamantylmaleimide. Polym Bull 36:59–65

    Article  CAS  Google Scholar 

  13. Jensen JJ, Grimsley M, Mathias LJ (1996) Adamantyl-substituted phenolic polymers. J Polym Sci Part A Polym Chem 34:397–402

    Article  CAS  Google Scholar 

  14. Lewis CM, Mathias LJ (1997) Preliminary evaluation of polyesters with pendent adamantyl groups synthesized from 5-adamantylisophthalic acid and 1,4-butanediol. Polym Bull 39:15–20

    Article  CAS  Google Scholar 

  15. Mathias LJ, Lewis CM, Wiegel KN (1997) Poly(ether ether ketone)s and poly(ether sulfones) with pendent adamantyl groups. Macromolecules 30:5970–5975

    Article  CAS  Google Scholar 

  16. Ishizone T, Tajima H, Torimae H, Nakahama S (2002) Anionic polymerizations of 1-adamantyl methacrylate and 3-methacryloyloxy-1,1′-biadamantane. Macromol Chem Phys 202:2375–2384

    Article  Google Scholar 

  17. Kobayashi S, Matsuzawa T, Matsuoka S, Tajima H, Ishizone T (2006) Living anionic polymerizations of 4-(1-adamantyl)styrene and 3-(4-vinylphenyl)-1,1′-biadamantane. Macromolecules 39:5979–5986

    Article  CAS  Google Scholar 

  18. Seino H, Mochizuki A, Ueda M (1999) Synthesis of aliphatic polyimides containing adamantyl units. J Polym Sci Part A Polym Chem 37:3584–3590

    Article  CAS  Google Scholar 

  19. Pasini D, Low E, Fréchet JMJ (2000) Novel design of carbon-rich polymers for 193 nm microlithography: adamantane-containing cyclopolymers. Adv Mater 12:347–350

    Article  CAS  Google Scholar 

  20. Watanabe Y, Shibasaki Y, Ando S, Ueda M (2005) New negative-type photosensitive alkaline-developable semi-aromatic polyimides with low dielectric constants based on poly(amic acid) from aromatic diamine containing adamantyl units and alicyclic dianhydrides, a cross-linker, and a photoacid generator. Polym J 37:270–276

    Article  CAS  Google Scholar 

  21. Mark JE (1990) Silicon-containing polymers. In: Ziegler JM, Gordon FW (eds) Silicon-based polymer science. American Chemical Society, Washington, DC (Adv Chem Ser, vol 224, pp 47–90)

  22. Brook MA (2000) Silicon in organic, organometallic, and polymer chemistry (chapter 9). Wiley, New York

    Google Scholar 

  23. Choi KM, Rogers JA (2003) A photocurable poly(dimethylsiloxane) chemistry designed for soft lithographic molding and printing in the nanometer regime. J Am Chem Soc 125:4060–4061

    Article  CAS  Google Scholar 

  24. Dvornic PR, Lenz RW (1990) High temperature siloxane elastomers (chapter 2). Hüthig & Wepf, Basel

    Google Scholar 

  25. Pai Y–M, Weber WP (1987) 1,3-Adamantanyl dimethylsiloxane copolymers: preparation and properties. Appl Organomet Chem 1:171–176

    Article  CAS  Google Scholar 

  26. Otomo Y, Nagase Y, Nemoto N (2005) Synthesis and properties of novel poly(tetramethylsilnaphthylenesiloxane) derivatives. Polymer 46:9714–9724

    Article  CAS  Google Scholar 

  27. Nemoto N, Watanabe Y, Umemiya J, Otomo Y (2006) Synthesis and characterization of poly(tetramethyl-1,4-silphenylenesiloxane) derivatives with oxyethylene substituent on phenylene moiety. Polym Bull 57:661–670

    Article  CAS  Google Scholar 

  28. Sato I, Takeda S, Arai Y, Miwa H, Nagase Y, Nemoto N (2007) Synthesis and thermal characterization of novel poly(tetramethylsilanthrylenesiloxane) and poly(tetramethylsilphenanthrylenesiloxane) derivatives. Polym Bull 59:607–617

    Article  CAS  Google Scholar 

  29. Niwa Y, Kouno S, Sayama W, Nemoto N (2008) Synthesis and thermal characterization of novel poly(tetramethyl-1,3-silphenylenesiloxane) derivative with phenol moiety in the main chain. J Polym Sci Part A Polym Chem 46:692–701

    Article  CAS  Google Scholar 

  30. Zhang R, Pinhas AR, Mark JE (1997) Synthesis of poly(tetramethyl-m-silphenylenesiloxane), an elastomer of enhanced high-temperature stability. Macromolecules 30:2513–2515

    Article  CAS  Google Scholar 

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Acknowledgments

This work was partly supported by 2008 Research Grant of College of Engineering, Nihon University. The authors would like to appreciate Dr. Chuichi Watanabe and Dr. Tetsuro Yuzawa, Frontier Laboratories Ltd., for the contribution in GC/MS analyses; and Ms. Satoko Tokiwa as well as Ms. Nami Sugashima, Nihon University College of Engineering Worldwide Research Center for Advanced Engineering and Technology (NEWCAT), for performing NMR measurements.

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  1. Department of Materials Chemistry and Engineering, College of Engineering, Nihon University, Koriyama, Fukushima, 963-8642, Japan

    Yusuke Hattori & Nobukatsu Nemoto

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  1. Yusuke Hattori
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  2. Nobukatsu Nemoto
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Correspondence to Nobukatsu Nemoto.

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Hattori, Y., Nemoto, N. Synthesis and thermal characterization of novel poly(tetramethyl-1,3-silphenylenesiloxane) derivative bearing adamantyl moiety. Polym. Bull. 63, 497–507 (2009). https://doi.org/10.1007/s00289-009-0110-7

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  • DOI: https://doi.org/10.1007/s00289-009-0110-7

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