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Published in: Polymer Bulletin 6/2017

04-11-2016 | Original Paper

Syntheses and thermal properties of polyesters bearing a carbosilane repeating unit

Authors: Ayumu Karimata, Kozo Matsumoto, Takeshi Endo

Published in: Polymer Bulletin | Issue 6/2017

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Abstract

New polyesters bearing a carbosilane repeating unit (–C–Si(CH3)2–C–), 1a and 1b, and reference polyesters with the corresponding carbon-based units 2a and 2b were synthesized and evaluated to study the effect of the carbosilane segment on their thermal properties. DSC analysis revealed that 1a and 1b exhibited glass transition temperatures (T g) of −72.6 and 11.6 °C, respectively, which were lower than those of 2a and 2b (–53.2 °C for 2a and 63.6 °C for 2b), indicating that the substitution of carbon atoms on polyester backbone with silicone atoms is effective method to change the T g of polyesters. Furthermore, 1a and 1b showed good thermal stability (T d5 = 304 °C for 1a and 309 °C for 2a). These results indicate that carbosilane segment may be a promising soft segment for developing new polyester-based materials.

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Appendix
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Literature
1.
go back to reference Wicks ZW, Jones FN, Pappas SP, Wicks DA (2007) Organic coatings: science and technology, chapter 10, 3rd edn. Wiley, New YorkCrossRef Wicks ZW, Jones FN, Pappas SP, Wicks DA (2007) Organic coatings: science and technology, chapter 10, 3rd edn. Wiley, New YorkCrossRef
2.
go back to reference Ihre H, Hult A, Soderlind E (1996) Synthesis, characterization, and 1H NMR self-diffusion studies of dendritic aliphatic polyesters based on 2,2-bis (hydroxymethyl) propionic acid and 1,1,1-tris(hydroxyphenyl)ethane. J Am Chem Soc 118:6388–6395. doi:10.1021/ja954171t CrossRef Ihre H, Hult A, Soderlind E (1996) Synthesis, characterization, and 1H NMR self-diffusion studies of dendritic aliphatic polyesters based on 2,2-bis (hydroxymethyl) propionic acid and 1,1,1-tris(hydroxyphenyl)ethane. J Am Chem Soc 118:6388–6395. doi:10.​1021/​ja954171t CrossRef
3.
go back to reference Ihre H, Hult A, Fréchet JMJ, Gitsov I (1998) Double-stage convergent approach for the synthesis of functionalized dendritic aliphatic polyesters based on 2,2-bis(hydroxymethyl)propionic acid. Macromolecules 31:4061–4068. doi:10.1021/ma9718762 CrossRef Ihre H, Hult A, Fréchet JMJ, Gitsov I (1998) Double-stage convergent approach for the synthesis of functionalized dendritic aliphatic polyesters based on 2,2-bis(hydroxymethyl)propionic acid. Macromolecules 31:4061–4068. doi:10.​1021/​ma9718762 CrossRef
4.
6.
go back to reference Parrott MC, Marchington EB, Valliant JF, Adronov A (2005) Synthesis and properties of carborane-functionalized aliphatic polyester dendrimers. J Am Chem Soc 127:12081–12089. doi:10.1021/ja053730l CrossRef Parrott MC, Marchington EB, Valliant JF, Adronov A (2005) Synthesis and properties of carborane-functionalized aliphatic polyester dendrimers. J Am Chem Soc 127:12081–12089. doi:10.​1021/​ja053730l CrossRef
7.
go back to reference Ma X, Zhou Z, Jin E, Sun Q, Zhang B, Tang J, Shen Y (2013) Facile synthesis of polyester dendrimers as drug delivery carriers. Macromolecules 46:37–42. doi:10.1021/ma301849a CrossRef Ma X, Zhou Z, Jin E, Sun Q, Zhang B, Tang J, Shen Y (2013) Facile synthesis of polyester dendrimers as drug delivery carriers. Macromolecules 46:37–42. doi:10.​1021/​ma301849a CrossRef
13.
go back to reference Höglund A, Odelius K, Hakkarainen M, Albertsson AC (2007) Controllable degradation product migration from cross-linked biomedical polyester-ethers through predetermined alterations in copolymer composition. Biomacromolecules 8:2025–2032. doi:10.1021/bm070292x CrossRef Höglund A, Odelius K, Hakkarainen M, Albertsson AC (2007) Controllable degradation product migration from cross-linked biomedical polyester-ethers through predetermined alterations in copolymer composition. Biomacromolecules 8:2025–2032. doi:10.​1021/​bm070292x CrossRef
16.
18.
go back to reference Jones RG, Wataru A, Julian C (2000) Silicon-containing polymers, chapter 10. Kluwer Academic Publishers, The Netherlands, pp 247–321CrossRef Jones RG, Wataru A, Julian C (2000) Silicon-containing polymers, chapter 10. Kluwer Academic Publishers, The Netherlands, pp 247–321CrossRef
19.
go back to reference Birot M, Pillot JP, Dunogues J (1995) Comprehensive chemistry of polycarbosilanes, polysilazanes, and polycarbosilazanes as precursors of ceramics. Chem Rev 95:1443–1477. doi:10.1021/cr00037a014 CrossRef Birot M, Pillot JP, Dunogues J (1995) Comprehensive chemistry of polycarbosilanes, polysilazanes, and polycarbosilazanes as precursors of ceramics. Chem Rev 95:1443–1477. doi:10.​1021/​cr00037a014 CrossRef
20.
go back to reference Putzien S, Nuyken O, Kühn FE (2010) Functionalized polysilalkylene siloxanes (polycarbosiloxanes) by hydrosilylation—catalysis and synthesis. Prog Polym Sci 35:687–713CrossRef Putzien S, Nuyken O, Kühn FE (2010) Functionalized polysilalkylene siloxanes (polycarbosiloxanes) by hydrosilylation—catalysis and synthesis. Prog Polym Sci 35:687–713CrossRef
21.
go back to reference Interrante LV, Rathore JS (2010) Cyclolinear polycarbosilanes—a recent addition to the class of organosilicon polymers. Dalton Trans 39:9193–9202. doi:10.1039/C0DT00142B Interrante LV, Rathore JS (2010) Cyclolinear polycarbosilanes—a recent addition to the class of organosilicon polymers. Dalton Trans 39:9193–9202. doi:10.​1039/​C0DT00142B
23.
go back to reference Rittscher V, Gallei M (2015) A convenient synthesis strategy for microphase-separating functional copolymers: the cyclohydrocarbosilane tool box. Polym Chem 6:5653–5662. doi:10.1039/C5PY00065C CrossRef Rittscher V, Gallei M (2015) A convenient synthesis strategy for microphase-separating functional copolymers: the cyclohydrocarbosilane tool box. Polym Chem 6:5653–5662. doi:10.​1039/​C5PY00065C CrossRef
27.
go back to reference O’Malley J, Pacansky TJ, Stauffer W (1977) Synthesis and characterization of poly(hexamethylene sebacate)-poly(dimethylsiloxane) block copolymers. Macromolecules 10:1197–1199. doi:10.1021/ma60060a007 CrossRef O’Malley J, Pacansky TJ, Stauffer W (1977) Synthesis and characterization of poly(hexamethylene sebacate)-poly(dimethylsiloxane) block copolymers. Macromolecules 10:1197–1199. doi:10.​1021/​ma60060a007 CrossRef
30.
31.
go back to reference Rosa VM, Felisberti MI (2001) Unsaturated polyester resin modified with poly(organosiloxanes). I. Preparation, dynamic mechanical properties, and impact resistance. J Appl Polym Sci 81:3272–3279. doi:10.1002/app.1783 CrossRef Rosa VM, Felisberti MI (2001) Unsaturated polyester resin modified with poly(organosiloxanes). I. Preparation, dynamic mechanical properties, and impact resistance. J Appl Polym Sci 81:3272–3279. doi:10.​1002/​app.​1783 CrossRef
32.
go back to reference He J, Zhou L, Soucek MD, Wollyung KM, Wesdemiotis C (2007) UV-curable hybrid coatings based on vinylfunctionlized siloxane oligomer and acrylated polyester. J Appl Polym Sci 105:2376–2386. doi:10.1002/app.25709 CrossRef He J, Zhou L, Soucek MD, Wollyung KM, Wesdemiotis C (2007) UV-curable hybrid coatings based on vinylfunctionlized siloxane oligomer and acrylated polyester. J Appl Polym Sci 105:2376–2386. doi:10.​1002/​app.​25709 CrossRef
33.
go back to reference Burke DJ, Kawauchi T, Kade MJ, Leibfarth FA, Mcdearmon B, Wol M, Kierstead PH, Moon B, Hawker CJ (2012) Ketene-based route to rigid cyclobutanediol monomers for the replacement of BPA in high performance polyester. ACS Macro lett 1:1228–1232. doi:10.1021/mz300497m CrossRef Burke DJ, Kawauchi T, Kade MJ, Leibfarth FA, Mcdearmon B, Wol M, Kierstead PH, Moon B, Hawker CJ (2012) Ketene-based route to rigid cyclobutanediol monomers for the replacement of BPA in high performance polyester. ACS Macro lett 1:1228–1232. doi:10.​1021/​mz300497m CrossRef
35.
go back to reference Hoppens NC, Hudnall TW, Foster A, Booth CJ (2004) Aliphatic–aromatic copolyesters derived from 2,2,4,4-tetramethyl-1,3-cyclobutanediol. J Polym Sci Part A Polym Chem 42:3473–3478. doi:10.1002/pola.20197 CrossRef Hoppens NC, Hudnall TW, Foster A, Booth CJ (2004) Aliphatic–aromatic copolyesters derived from 2,2,4,4-tetramethyl-1,3-cyclobutanediol. J Polym Sci Part A Polym Chem 42:3473–3478. doi:10.​1002/​pola.​20197 CrossRef
36.
go back to reference Whitney JM, Parnes JS, Shea KJ (1997) Total synthesis of a Plocamium monoterpene marine natural product. Synthetic applications of bridgehead allylsilanes. J Org Chem 62:8962–8963. doi:10.1021/jo971580u CrossRef Whitney JM, Parnes JS, Shea KJ (1997) Total synthesis of a Plocamium monoterpene marine natural product. Synthetic applications of bridgehead allylsilanes. J Org Chem 62:8962–8963. doi:10.​1021/​jo971580u CrossRef
37.
go back to reference Evangelisti C, Klapötke TM, Krumm B, Nieder A, Berger RJF, Hayes SA, Mitzel NW, Troegel D, Tacke R (2010) Sila-substitution of alkyl nitrates: synthesis, structural characterization, and sensitivity studies of highly explosive (nitratomethyl)-, bis(nitratomethyl)-, and tris(nitratomethyl)silanes and their corresponding carbon analogues. Inorg Chem 49:4865–4880. doi:10.1021/ic902387y CrossRef Evangelisti C, Klapötke TM, Krumm B, Nieder A, Berger RJF, Hayes SA, Mitzel NW, Troegel D, Tacke R (2010) Sila-substitution of alkyl nitrates: synthesis, structural characterization, and sensitivity studies of highly explosive (nitratomethyl)-, bis(nitratomethyl)-, and tris(nitratomethyl)silanes and their corresponding carbon analogues. Inorg Chem 49:4865–4880. doi:10.​1021/​ic902387y CrossRef
Metadata
Title
Syntheses and thermal properties of polyesters bearing a carbosilane repeating unit
Authors
Ayumu Karimata
Kozo Matsumoto
Takeshi Endo
Publication date
04-11-2016
Publisher
Springer Berlin Heidelberg
Published in
Polymer Bulletin / Issue 6/2017
Print ISSN: 0170-0839
Electronic ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-016-1834-9

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