Summary
Novel poly(tetramethyl-1,4-silphenylenesiloxane) derivatives having 2-methoxy-ethoxy or 2-(2-methoxyethoxy)ethoxy substituents at both 2- and 5-positions on phenylene moieties were synthesized and characterized by differential scanning calorimetry and thermogravimetry analyses. Poly(tetramethyl-1,4-silphenylene-siloxane) derivatives were obtained by condensation polymerization of the corresponding disilanol derivatives, i.e., 1,4-bis(dimethylhydroxysilyl)-2,5-bis(2-methoxyethoxy)benzene and 1,4-bis(dimethylhydroxysilyl)-2,5-bis[2-(2-methoxy-ethoxy)ethoxy]benzene, which were prepared by the Grignard reaction using chlorodimethylsilane and the corresponding dibromobenzene derivatives followed by the hydrolyses, catalyzed by palladium on charcoal. The introduction of 2-methoxyethoxy groups on the phenylene moiety made the melting point high, compared with poly(tetramethyl-1,4-silphenylenesiloxane); however, that of 2-(2-methoxyethoxy)ethoxy groups made it low, indicating the longer oxyethylene moiety induced the lowering of the melting point. There were no significant differences in the thermostabilities of both present polymers, suggesting the length of oxyethylene moiety would not affect the thermostability, though the introduction of polar oxyethylene group onto the phenylene moiety induced a decline of thermostability.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
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)
Brook MA (2000) Silicon in organic, organometallic, and polymer chemistry (chapter 9). John Wiley & Sons, Inc, New York
Dvornic PR, Lenz RW (1990) High temperature siloxane elastomers (chapter 2). Hüthig & Wepf Verlag, Basel, Heiderberg, New York
Day GM, Hibberd AI, Habsuda J, Sharp GJ (2003) Thermally stable siloxane polymers for gas chromatography. In: Clarson SJ, Fitzgerald JJ, Owen MJ, Smith SD, van Dyke ME (eds) Synthesis and properties of silicones and silicone-modified materials. American Chemical Society, Washington DC (ACS Symp Ser vol 838, pp 127-136)
Merker RL, Scott MJ (1964) J Polym Sci: Part A 2: 15-29
Beck HN, Chaffee RG (1963) J Chem Eng Data 8: 602-3
Nagase Y, Nakamura T, Misawa A, Ikeda K, Sekine Y (1983) Polymer 24: 457-62
Nagase Y, Ochiai J, Matsui K, Uchikura M (1988) Polymer 29: 740-5
Dvornic PR, Lenz RW (1994) Macromolecules 27: 5833-8
Loree LA, Brown ED (1971) US Patent, 3, 576, 020
Grindhal GA (1971) US Patent, 3, 576, 021
Pelter A, Jenkins I, Jones DE (1997) Tetrahedron 30: 10357-400
(a) Ouchi M, Inoue Y, Wada K, Iketani S, Hakushi T, Weber E (1987) J Org Chem 52: 2420-7 (b) Ouchi M, Inoue Y, Kanzaki T, Hakushi T (1984) J Org Chem 49: 1408-12
Barnes Jr GH, Daughenbaugh NE (1966) J Org Chem 31: 885-7
Li HM, Magill JH (1978) J Polym Sci: Polym Phys Ed 16: 1059-70
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Open Access This is an open access article distributed under the terms of the Creative Commons Attribution Noncommercial License ( https://creativecommons.org/licenses/by-nc/2.0 ), which permits any noncommercial use, distribution, and reproduction in any medium, provided the original author(s) and source are credited.
About this article
Cite this article
Nemoto, N., Watanabe, Y., Umemiya, J. et al. Synthesis and Characterization of Poly(tetramethyl-1,4-silphenylenesiloxane) Derivatives with Oxyethylene Substituent on Phenylene Moiety. Polym. Bull. 57, 661–670 (2006). https://doi.org/10.1007/s00289-006-0644-x
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-006-0644-x