Modern Approaches to Obtaining Organofunctional Silsesquioxanes
- Authors: Bredov N.S.1, Kireev V.V.1, Polyakov V.A.1, Sokol’skaya I.V.2, Esin A.S.1
-
Affiliations:
- Mendeleev University of Chemical Technology
- State Research Institute of Chemistry and Technology of Organoelement Compounds
- Issue: Vol 65, No 2 (2023)
- Pages: 193-209
- Section:
- URL: https://journals.rcsi.science/2308-1147/article/view/232911
- DOI: https://doi.org/10.31857/S2308114723700358
- EDN: https://elibrary.ru/YEFWCF
- ID: 232911
Cite item
Abstract
Modern research in the field of synthesis of organofunctional oligosilsesquioxanes is considered. Relationships between the composition and structure of oligomeric organosilsesquioxanes and the conditions for their formation during the hydrolytic and acidohydrolytic polycondensation of organotrialkoxysilanes containing various functionalities, such as methacrylic, aminopropyl, carboxyl, and cyclotriphosphazene groups, in organic radicals bonded to silicon atoms are shown. A comparative analysis of approaches to the synthesis of organofunctional incompletely condensed oligosilsesquioxanes has been carried out.
About the authors
N. S. Bredov
Mendeleev University of Chemical Technology
Email: koljabs@rambler.ru
125047, Moscow, Russia
V. V. Kireev
Mendeleev University of Chemical Technology
Email: koljabs@rambler.ru
125047, Moscow, Russia
V. A. Polyakov
Mendeleev University of Chemical Technology
Email: koljabs@rambler.ru
125047, Moscow, Russia
I. V. Sokol’skaya
State Research Institute of Chemistry and Technology of Organoelement Compounds
Email: koljabs@rambler.ru
111123, Moscow, Russia
A. S. Esin
Mendeleev University of Chemical Technology
Author for correspondence.
Email: koljabs@rambler.ru
125047, Moscow, Russia
References
- Dudziec B., Zak P., Marciniec B. // Polymers. 2019. V. 11. P. 504.
- Bassindale A.R., Pourny M., Taylor P.G., Hursthouse M.B., Light M.E. // Angew. Chem. 2003. V. 115. № 30. P. 3612.
- Fina A., Tabuani D., Carniato F., Frache A., Boccaleri E., Camino G. // Thermochim. Acta. 2006. V. 440. № 1. P. 36.
- Hurkes N., Bruhn C., Belaj F., Pietschnig R. // Organometallics. 2014. V. 33. № 24. P. 7299.
- Chimjarn S., Kunthom R., Chancharone P., Sodkhomkhum R., Sangtrirutnugul P., Ervithayasuporn V. // Dalton Trans. 2015. V. 44. № 3. V. 916.
- Unno M., Suto A., Matsumoto T. // Russ. Chem. Rev. 2013. V. 82. № 4. P. 289.
- Zhang W., Camino G., Yang R. // Prog. Polym. Sci. 2017. V. 67. P. 77.
- Mori H. // Int. J. Polym. Sci. 2012. V. 2012. Art. ID 173624.
- Oleksy M., Galina H. // Ind. Eng. Chem. Res. 2013. V. 52. № 20. P. 6713.
- Bandyopadhyay P., Banerjee S. // Ind. Eng. Chem. Res. 2014. V. 53. № 47. P. 18273.
- Liu H., Zheng S. // Macromol. Rapid Commun. 2005. V. 26. № 3. P. 196.
- Han Z., Xi Y., Kwon Y. // J. Nanosci. Nanotechnol. 2016. V. 16. № 2. P. 1928.
- Abbasi M.R., Karimi M., Atai M. // Dent. Mater. 2021. V. 37. № 8. P. 1283.
- Lian X., Shi D., Ma J., Cai X., Gu Z. // Chin. Chem. Lett. 2018. V. 29. № 3. P. 501.
- Acar S.B., Tasdelen M.A., Karaagac B. // Iran. Polym. J. 2021. V. 30. № 7. P. 697.
- Liu L., Zhang W., Yang R. // Polym. Adv. Technol. 2020. V. 31. № 9. P. 2058.
- Zhao F., Huang Y. // J. Mater. Chem. 2011. V. 21. № 11. P. 3695.
- Zhang C., Wu G., Jiang H. // Compos. A. 2018. V. 109. P. 555.
- Wu G., Chen L., Liu L. // J. Mater. Sci. 2017. V. 52. № 2. P. 1057.
- Xu W., Hao L., An Q., Wang X. // J. Polym. Res. 2015. V. 22. № 2. P. 20.
- Li L., Feng S., Liu H. // RSC Adv. 2014. V. 4. № 74. P. 39132.
- Blanco I., Abate L., Bottino F.A. // J. Therm. Anal. Calorim. 2013. V. 112. № 1. P. 421.
- Knauer K.M., Brust G., Carr M., Cardona R.J., Lichtenhan J.D., Morgan S.E. // J. Appl. Polym. Sci. 2017. V. 134. № 7. P. 44462.
- Yuasa S., Sato Y., Imoto H., Naka K. // J. Appl. Polym. Sci. 2018. V. 135. № 12. P. 46033.
- Igarashi A., Ueda Y., Katoh R., Imoto H., Naka K. // J. Polym. Sci. 2021. V. 59. № 2. P. 131.
- Wu X., Sun Y., Xie W., Liu Y., Song X. // Dent. Mater. 2010. V. 26. № 5. P. 456.
- Burujeny S.B., Yeganeh H., Atai M., Gholami H., Sorayya M. // Dent. Mater. 2017. V. 33. № 1. P. 119.
- Zelmer C., Wang D.K., Keen I., Hill D.J.T., Symons A.L., Walsh L.J., Rasoul F. // Dent. Mater. 2016. V. 32. № 4. P. e82.
- Emerging Nanotechnologies in Dentistry (sec. ed.) / Eds by S. Karthikeyan, A. Waqar. Amsterdam: Elsevier, 2018.
- Canellas T.A.T., de Almeida Neves A., dos Santos I.K.B., de Rezende A.R.P., Fellows C.E., da Silva E.M. // J. Mech. Behav. Biomed. Mater. 2019. V. 90. P. 566.
- Pramudya I., Rico C.G., Lee C., Chung H. // Biomacromolecules. 2016. V. 17. № 12. P. 3853.
- Du Y., Liu H. // Dalton Trans. 2020. V. 49. № 17. P. 5396.
- Loman-Cortes P., Binte Huq T., Vivero-Escoto J.L. // Molecules. 2021. V. 26. № 21. P. 6453.
- Ghanbari H., Cousins B.G., Seifalian A.M. // Macromol. Rapid Commun. 2011. V. 32. № 14. P. 1032.
- Naderi N., Madani S.Y., Mosahebi A., Seifalian A.M. // Nano Reviews. 2015. V. 6. № 1. P. 28297.
- Feher J.F., Wyndham D.K., Soulivong D., Nguyen F. // J. Chem. Soc., Dalton Trans. 1999. № 9. P. 1491.
- Fabritz S., Heyl D., Bagutski V., Empting M., Rikowski E., Frauendorf H., Balog I., Fessner W.-D., Schneider J.J., Jorg J., Avrutina O., Kolmar H. Towards // Org. Biomol. Chem. 2010. V. 8. № 9. P. 2212.
- Heyl D., Rikowski E., Hoffmann R.C., Schneider J.J., Fessner W.-D. // Chem. Eur. J. 2010. V. 16. № 19. P. 5544.
- Kim Y.-J., Lee H.-I., Kim J.-K., Kim C.-H., Kim Y.-J. // Colloids Surf. B. 2020. V. 189. P. 110829.
- Wang K., Peng H., Thurecht K.J., Whittaker A.K. // Macromol. Chem. Phys. 2016. V. 217. P. 2262.
- Strauch H., Engelmann J., Scheffler K., Mayer H.A. // Dalton Trans. 2016. V. 45. № 38. P. 15104.
- Chen M., Zhang Y., Xie Q., Zhang W., Pan X., Gu P., Zhou H., Gao Y., Walther A., Fan X. // ACS Biomater. Sci. Eng. 2019. V. 5. № 9. P. 4612.
- Chatterjee S., Ooya T. // Materials. 2019. V. 12. № 7. P. 1058.
- Ivanov A.G., Kopylov V.M., Ivanova V.L., Kovyazin V.A., Sokol’skaya I.B., Khazanov I.I. // Russ. J. Gen. Chem. 2012. V. 82. № 1. P. 66.
- Bredov N.S., Shporta E.Yu., Liu Y., Kireev V.V., Bori-sov R.S., Gorlov M.V., Posokhova V.F., Chuev V.P. // Polymer Science B. 2013. V. 55. № 7–8. P. 472.
- Ivanov A.G., Kopylov V.M., Kireev V.V., Borisov R.S., Gerasimov K.L., Bilichenko Yu.V. // Polymer Science B. 2015. V. 57. № 1. P. 9.
- Kalinina A., Strizhiver N., Vasilenko N., Perov N., Demchenko N., Muzafarov A. // Silicon. 2015. V. 7. № 2. P. 95.
- Bychkova A.A., Soskov F.V., Demchenko A.I., Storozhenko P.A., Muzafarov A.M. // Russ. Chem. Bull. 2011. V. 60. № 11. P. 2384.
- Tatarinova E., Vasilenko N., Muzafarov A. // Molecules. 2017. V. 22. P. 1768.
- Drozdov F.V., Krapivko A.L., Cherkaev G.V., Gervits L.L., Yashtulov N.A., Kalinina A.A., Muzafarov A.M. // J. Organomet. Chem. 2020. V. 921. P. 121398.
- Kalinina A.A., Talalaeva E.V., Demchenko A.I., Vasilenko N.G., Molodtsova Yu.A., Demchenko N.V., Muza-farov A.M. // Russ. Chem. Bull. 2016. V. 65. № 4. P. 1013.
- Soldatov M.A., Sheremetyeva N.A., Serenko O.A., Muzafarov A.M. // Silicon 2015. V. 7. № 2. P. 211.
- Shkinev P., Evdokimova A., Drozdov F.V., Gervits L.L., Muzafarov A.M. // J. Organomet. Chem. 2021. V. 948. P. 121910.
- Bredov N.S., Shporta E.Yu., Gorlov M.V., Kireev V.V., Filatov S.N., Posokhova V.F., Chuev V.P. // Polymer Science B. 2015. V. 57. № 5. P. 444.
- Bredov N.S., Soan L.P., Kireev V.V., Bykovskaya A.A., Sokol’skaya I.B., Gorlov M.V., Esin A.S., Bekmukhamedova S.R., Polyakov V.A. // Polymer Science B. 2017. V. 59. № 3. P. 240.
- Bredov N.S., Soan L.P., Kireev V.V., Bykovskaya A.A., Sokol’skaya I.B., Posokhova V.F., Klyukin B.V., Chuev V.P. // Russ. J. Appl. Chem. 2017. V. 90. № 4. P. 595.
- Bredov N.S., Bykovskaya A.A., Van Tuan N., Kireev V.V., Tupikov A.S., Sokol’skaya I.B., Posokhova V.F., Chuev V.P. // Polymer Science B. 2020. V. 62. № 3. P. 182.
- Kireev V.V., Posokhova V.F., Sokol’skaya I.B., Chuev V.P., Dyatlov V.A., Filatov S.N. // Polymer Science B. 2008. V. 50. № 3–4. P. 101.
- Bredov N.S., Nguyen V.T., Zaitseva D.S., Kireev V.V., Gorlov M.V., Sokol’skaya I.B., Polyakov V.A. // Polymer Science B. 2021. V. 63. № 4. P. 341.
- Нгуен В.Т. Дис. … канд. хим. наук. М.: РХТУ им. Д.И. Менделеева, 2021.
- Bredov N.S., Nguyen V.T., Zaitseva D.S., Kireev V.V., Gorlov M.V., Sokol’skaya I.B., Polyakov V.A. // Polymer Science B. 2021. V. 63. № 4. P. 350.
- Бредов Н.С. Дис. …канд. хим. наук. М.: РХТУ им. Д.И. Менделеева, 2011.
- van De Grampel J.C., Jekel A.P., Puyenbroek R., Arling T.J., Faber M.C., Fransen W., Meetsma A., Wübbels J.H. // Phosphorus, Sulfur Silicon Relat. Elem. 1993. V. 76. № 1–4. P. 215.
- Kireev V.V., Bredov N.S., Prudskov B.M., Mu J., Bo-risov R.S., Sokol’skaya I.B., Chuev V.P. // Polymer Science B. 2011. V. 53. № 1–2. P. 64.
- Zaikin V.G., Borisov R.S., Polovkov N.Yu., Filatov S.N., Kireev V.V. // Eur. J. Mass. Spectrom. 2009. V. 15. № 2. P. 231.
- Cai H., Zhang X., Xu K., Liu H., Su J., Liu X., Fu Y., Chen M. // Polym. Adv. Technol. 2012. V. 23. № 4. P. 765.
- Peng J., Xu K., Cai H., Wu J., Lin W., Yu Z., Chen M. // RSC Adv. 2014. V. 4. № 14. P. 7124.
- Oben D.T. PhD Thesis. Milton Keynes (UK): The Open University, 2016.
- Dutkiewicz M., Maciejewski H., Marciniec B. // Synthesis. 2009. V. 2009. № 12. P. 2019.
- Ervithayasuporn V., Chimjarn S. // Inorg. Chem. 2013. V. 52. № 22. P. 13108.
- Nishiyama N., Horie K., Asakura T. // J. Appl. Polym. Sci. 1987. V. 34. № 4. P. 1619.
- Smith K.A. // Macromolecules. 1987. V. 20. № 10. P. 2514.
- Abe Y., Gunji T. // Prog. Polym. Sci. 2004. P. 29. № 3. P. 149.
- Brochier Salon M.-C., Bardet M., Belgacem M.N. // Silicon Chem. 2008. V. 3. № 6. P. 335.
- Hoebbel D., Engelhardt G., Samoson A., Ujszaszy K., Smolin Yu.I. // Z. Anorg. Allg. Chem. 1987. V. 552. № 9. P. 236.
- Unno M., Suto A., Takada K., Matsumoto H. // Bull. Chem. Soc. Jpn. 2000. V. 73. № 1. P. 215.
- Spirk S., Nieger M., Belaj F., Pietschnig R. // Dalton Trans. 2009. № 1. P. 163.
- Unno M., Alias S.B., Saito H., Matsumoto H. // Organometallics. 1996. V. 15. № 9. P. 2413.
- Kahr J., Belaj F., Pietschnig R. // Inorganics. 2017. V. 5. № 4. P. 66.
- Choi S.-S., Lee A.S., Hwang S.S., Baek K.-Y. // Macromolecules. 2015. V. 48. № 17. P. 6063.
- Abe Y., Gunji A., Arimitsu K. Pat. 2007015991A JP. 2007.
- Song Y.L., Choi J.Y., Lee M.H. Pat. 10501583B2 USA, 2019.
- Allcock H.R. // Dalton Trans. 2016. V. 45. № 5. P. 1856.
- Allcock H.R., Morozowich N.L. // Polym. Chem. 2012. V. 3. № 3. P. 578.
- Khan R.U., Wang L., Yu H., Zain-ul-Abdin, Akram M., Wu J., Haroon M., Ullah R.S., Deng Z., Xia X. // Russ. Chem. Rev. 2018. V. 87. № 2. P. 109.
- Allcock H.R., Coggio W.D. // Macromolecules. 1990. V. 23. № 6. P. 1626.
- Tong C., Tian Z., Chen C., Li Z., Modzelewski T., Allcock H.R. // Macromolecules. 2016. V. 49. № 4. P. 1313.
- Allcock H.R., Prange R. // Macromolecules. 2001. V. 34. № 20. P. 6858.
- Cassagneau T., Jones D.J., Roziere J. // J. Phys. Chem. 1993. V. 97. P. 8678.
- Olivera-Pastor P., Maireles-Torres P., Rodriguez-Castellon E., Jimenez-Lopez A., Cassagneau T., Jones J., Roziere J. // Chem. Mater. 1996. V. 8. № 8. P. 1758.
- Feher F.J., Wyndham K.D. // Chem. Commun. 1998. № 3. P. 323.
- Gravel M.-C., Zhang C., Dinderman M., Laine R.M. // Appl. Organometal. Chem. 1999. V. 13. № 4. P. 329.
- Yanagie M., Kaneko Y. // Polym. Chem. 2018. V. 9. № 17. P. 2302.
- Matsumoto T., Kaneko Y. // Bull. Chem. Soc. Jpn. 2019. V. 92. № 6. P. 1060.
- Matsumoto T., Kaneko Y. // J. Sol-Gel Sci. Technol. 2020. V. 95. № 3. P. 670.
- Kummari S.V.K.R., Kummara M.R., Palem R.R., Nagellea S.R., Shchipunov Y., Ha C.-S. // Polym. Int. 2015. V. 64. № 2. P. 293.
- Liu S., Lang X., Ye H., Zhang S., Zhao J. // Eur. Polym. J. 2005. V. 41. № 5. P. 996.
- John L., Janeta M., Rajczakowska M., Ejfler J., Lydzba D., Szafert S. // RSC Adv. 2016. V. 6. № 70. P. 66037.
- John L., Janeta M., Szafert S. // New J. Chem. 2018. V. 42. № 1. P. 39.
- Konuray A.O., Fernandez-Francos X., Serra A., Ramis X. // Eur. Polym. J. 2016. V. 84. P. 256.
- Gomez M.L., Fasce D.P., Williams R.J.J., Erra-Balsells R., Kaniz Fatema M., Nonami H. // Polymer. 2008. V. 49. № 17. P. 3648.
- Muh E., Marquardt J., Klee J.E., Frey H., Mulhaupt R. // Macromolecules. 2001. V. 34. № 17. P. 5778.
- Moszner N., Volkel T., von Clausbruch S.C., Geiter E., Batliner N., Rheinberger V. // Macromol. Mater. Eng. 2002. V. 287. № 5. P. 339.
- Kireev V.V., Chistyakov E.M., Filatov S.N., Tupikov A.S., Panfilova D.V., Chetverikova A.I. // Russ. J. Appl. Chem. 2015. V. 88. № 5. P. 866.
- Diaz-Garcia D., Ardiles P., Prashar S., Rodriguez-Dieguez A., Paez P., Gomez-Ruiz S. // Pharmaceutics. 2019. V. 11. № 1. P. 30.
- Jiang Z., Yuan L., Liang G., Gu A. // Polym. Degrad. Stab. 2015. V. 121. P. 30.
- Schafer S., Kickelbick G. // Polymer. 2015. V. 69. P. 357.
- Proupin-Perez M., Cosstick R., Liz-Marzan L.M., Salgueirino-Maceira V., Brust M. // Nucleosides Nucleotides Nucleic Acids. 2005. V. 24. № 5–7. P. 1075.
- Lu G.T., Huang Y. // J. Mater. Sci. 2002. V. 37. P. 2305.
- Kovyazin V.A., Nikitin A.V., Kopylov V.M., Sokol’skaya I.B. // Russ. J. Gen. Chem. 2003. V. 73. № 7. P. 1072.
- Kovyazin V.A., Nikitin A.V., Kopylov V.M., Sokol’skaya I.B. // Russ. J. Gen. Chem. 2007. V. 77. № 1. P. 47.
- Egorova E.V., Vasilenko N.G., Demchenko N.V., Tatarinova E.A., Muzafarov A.M. // Dokl. Chem. 2009. V. 424. № 1. P. 15.
- Abakumov G.A., Piskunov A.V., Cherkasov V.K., Fedushkin I.L., Ananikov V.P., Eremin D.B., Gordeev E.G., Beletskaya I.P., Averin A.D., Bochkarev M.N., Trifonov A.A., Dzhemilev U.M., D’yakonov V.A., Egorov M.P., Vereshchagin A.N., Syroeshkin M.A., Jouikov V.V., Muzafarov A.M., Anisimov A.A., Arzumanyan A.V., Kononevich Y.N., Temnikov M.N., Sinyashin O.G., Budnikova Y.H., Burilov A.R., Karasik A.A., Mironov V.F., Storozhenko P.A., Shcherbakova G.I., Trofimov B.A., Amosova S.V., Gusarova N.K., Potapov V.A., Shur V.B., Burlakov V.V., Bogdanov V.S., Andreev M.V. // Russ. Chem. Rev. 2018. V. 87. № 5. P. 393.
- Muzafarov A.M., Bystrova A.V., Vasilenko N.G., Ignat’eva G.M. // Russ. Chem. Rev. 2013. V. 82. № 7. P. 635.
- Sapozhnikov D.A., Vygodskii Ya.S. // Polymer Science B. 2015. V. 57. № 4. P. 275.
- Soldatov M.A., Sheremet’eva N.A., Kalinina A.A., Demchenko N.V., Serenko O.A., Muzafarov A.M. // Russ. Chem. Bull. 2014. V. 63. № 1. P. 267.
- Borisov K.M., Kalinina A.A., Bokova E.S., Ilyina M.N., Cherkaev G.V., Tatarinova E.A., Milenin S.A., Bystrova A.V., Moeller M., Muzafarov A.M. // Mendeleev Commun. 2022. V. 32. № 2. P. 164.
- Шпорта Е.Ю. Дис. … канд. хим. наук. М.: РХТУ им. Д.И. Менделеева, 2014.
- Asmussen S.V., Giudicessi S.L., Erra-Balsells R., Vallo C.I. // Eur. Polym. J. 2010. V. 46. № 9. P. 1815.
- Imai K., Kaneko Y. // Inorg. Chem. 2017. V. 56. № 7. P. 4133.
- Kaneko Y., Shoiriki M., Mizumo T. // J. Mater. Chem. 2012. V. 22. № 29. P. 14475.