Abstract
New polymeric products containing cyclopropane groups in the macromolecules have been obtained by catalytic cyclopropanation of syndiotactic 1,2-PB with diazomethane. A comparative estimate of the activity and regioselectivity of the catalysts used in the 1,2-PB cyclopropanation is given. It has been shown that varying the catalyst nature allows one to control the cyclopropanation process and to obtain modified polymers with predefined structure and degree of functionalization. The effect of the degree of modification on the molecular characteristics and properties of cyclopropanated polymers, such as viscosity of solutions and melts, glass transition point, crystallinity and thermal stability, has been studied. It has been shown that the incorporation of cyclopropane groups into macromolecules of syndiotactic 1,2-PB gives amorphous thermoplastic polymeric products that are rather energy rich and are of practical interest.
Similar content being viewed by others
References
Mohanty AD, Bae C (2015) Transition metal-catalyzed functionalization of polyolefins containing C–C, C=C, and C–H bonds. Adv Organomet Chem 64:1–39. https://doi.org/10.1016/bs.adomc.2015.08.002
Rodgers B (2015) Rubber compounding: chemistry and applications, 2nd edn. CRC Press, Boca Raton
Abdullin MI, Glazyrin AB, Kukovinets OS, Basyrov AA, Zaikov GE (2016) Chemical transformation of syndiotactic 1,2-polybutadiene. In: Process advancement in chemistry and chemical engineering research, chapter 7. Apple Academic Press. https://doi.org/10.1201/b19839-8
Abdullin MI, Glazyrin AB, Kukovinets OS, Basyrov AA, Zaikov GE (2015) Chemical modification of syndiotactic 1,2-polybutadiene. In: Mechanical and physico-chemical characteristics of modified materials, chapter 3. Apple Academic Press. https://doi.org/10.1201/b18708-2
Abdullin MI, Glazyrin AB, Kukovinets OS, Basyrov AA, Zaikov GE (2015) Chemical modification of syndiotactic 1,2-polybutadiene. In: The chemistry and physics of engineering materials, chapter 1. Apple Academic Press
Glazyrin AB, Abdullin MI, Kukovinets OS, Basyrov AA, Zaikov GE (2015) Chemical modification of syndiotactic 1,2-polybutadiene. Nonlinear Opt Quantum Opt 47:85–101
Glazyrin AB, Abdullin MI, Kukovinets OS (2009) Syndiotactic 1,2-polybutadiene: properties and chemical modification. Vestn Bashkirskogo Univ 14:1133–1140
Abdullin MI, Basyrov AA, Glazyrin AB, Kukovinets OS, Muslukhov RR (2012) Chemical modification of syndiotactic 1,2-polybutadiene. Izvestiya Vysshikh Uchebnykh Zavedeniy. Khimiya i khimicheskaya tekhnologiya 55:71–78
Kukovinets OS, Glazyrin AB, Basyrov AA, Dokichev VA, Abdullin MI (2013) Achievements in chemical modification of syndiotactic 1,2-polybutadiene. Izvestiya Ufimskogo nauchnogo tsentra RAN 1:29–37
Abdullin MI, Glazyrin AB, Asfandiyarov RN, Akhmetova VR (2006) Synthesis and properties of halo derivatives of syndiotactic 1,2-polybutadiene. Plast Massy 11:20–23
Glazyrin AB, Abdullin MI, Muslukhov RR, Kraikin VA (2011) Hydrochlorinated derivatives of syndiotactic 1,2-polybutadiene. Polym Sci Ser A 53:110–115. https://doi.org/10.1134/S0965545X11020040
Glazyrin AB, Abdullin MI, Asfandiyarov RN, Akhmetova VR, Zaboristov VN (2006) Chlorine derivatives of syndiotactic 1,2-polybutadiene. Polym Sci Ser B 48:104–107. https://doi.org/10.1134/S1560090406030122
Glazyrin AB, Abdullin MI, Muslukhov RR (2012) Dichlorocyclopropane derivatives of syndiotactic 1,2-polybutadiene. Polym Sci Ser B 54:234–239. https://doi.org/10.1134/S1560090412030062
Glazyrin AB, Abdullin MI, Dokichev VA, Sultanova RM, Muslukhov RR, Yangirov TA (2013) Synthesis and properties of cyclopropane derivatives of polybutadienes. Polym Sci Ser B 55:651–656. https://doi.org/10.1134/S1560090413080034
Glazyrin AB, Abdullin MI, Dokichev VA, Sultanova RM, Muslukhov RR, Gazizova ER (2014) Derivatives of syndiotactic cyclopropane-containing 1,2–polybutadiene. Polym Sci Ser B 56:807–813. https://doi.org/10.7868/S2308113914060072
Glazyrin AB, Abdullin MI, Gazizova ER (2015) Properties of dichlorocyclopropane derivatives of syndiotactic 1,2-polybutadiene. Russ J Appl Chem 88(3):473–479. https://doi.org/10.1134/S1070427215030179
Glazyrin AB, Abdullin MI, Gazizova ER, Dokichev VA, Sultanova RM, Zaikov GE (2015) Cyclopropane derivatives of syndiotactic 1,2-polybutadiene. J Nat Sci Sustain Technol 9:331–339
Glazyrin AB, Abdullin MI, Zaikov GE (2015) Synthesis and properties of dichlorocyclopropane derivatives of syndiotactic 1,2-polybutadiene. J Nat Sci Sustain Technol 9:297–306
Glazyrin AB, Abdullin MI, Kukovinets OS, Basyrov AA (2015) Chemical modification of syndiotactic 1,2-polybutadiene, chapter 3. Apple Academic Press, Oakville, pp 21–37
Abdullin MI, Glazyrin AB, Kukovinets OS, Basyrov AA, Khamidullina GI (2014) Epoxidation of syndiotactic 1,2-polybutadiene with peroxy acids. Izvestiya Vysshikh Uchebnykh Zavedeniy. Khimiya i khimicheskaya tekhnologiya 57:54–58
Glazyrin AB, Abdullin MI, Biktashev IA (2013) Modified adhesive formulations for sticky PVC tape containing halogenated 1,2-polybutadienes. Plast Massy 3:48–50
Abdullin MI, Glazyrin AB, Kukovinets OS, Basyrov AA, Khamidullina GI (2014) Patent RU 2,516,491 C1
Lenhardt JM, Black AL, Craig SL (2009) gem-Dichlorocyclopropanes as abundant and efficient mechanophores in polybutadiene copolymers under mechanical stress. J Am Chem Soc 131:10818–10819. https://doi.org/10.1021/ja9036548
Lenhardt JM, Black AL, Beiermann BA, Steinberg BD, Rahman F, Samborski T, Elsakr J, Moore JS, Sottos NR, Craig SL (2011) Characterizing the mechanochemically active domains in gem-dihalocyclopropanated polybutadiene under compression and tension. J Mater Chem 21:8454–8459. https://doi.org/10.1039/c0jm04117c
Kaspar M, Bubnov A, Sedláková Z, Stojanović M, Havlíček J, Obadović DZ, Ilavský M (2008) Liquid crystalline polybutadiene diols with chiral thiol side-chain units. Eur Polymer J 44:233–243. https://doi.org/10.1016/j.eurpolymj.2007.10.014
Polakova L, Sedlakova Z, Látalová P (2010) Synthesis and thermal behavior of telechelic poly(butadiene)diols with azobenzene-based liquid-crystalline units in side chains. Polym Bull 64:315–326. https://doi.org/10.1007/s00289-009-0142-z
Abdullin MI, Glazyrin AB, Kinzibaev DR, Basyrov AA (2015) Patent RU 2,563,259 C1
Abdullin MI, Glazyrin AB, Kinzibaev DR (2016) Patent RU 2,587,450 C1
Dzhemilev UM, Popod’ko NR, Kozlova EV (1999) Transition metal catalysis in organic synthesis. Khimiya, Moscow (in Russian)
Kazanskii BA, Plate AF (1949) Syntheses of organic compounds. Izdatel’stvo inostrannoi literatury (Foreign literature publishing house), Moscow
Tager AA (2007) Physical chemistry of polymers. Nauchnyi Mir, Moscow (in Russian)
Chapko TA, Chernov MA, Goldobin SF (2003) Patent RU 2,216,008 C1
Grell’mann V, Zaidler S (2010) Testing of plastics. TsOP Professiya, St. Petersburg
Laput’ko BN, Savel’ev AP (1994) Plotting a generalized dependence of the viscosity of melts of filled PVC formulations on shear velocity. Plast Massy 3:31–34
Rafikov SR, Budtov VP, Monakov YuB (1978) Introduction to the physical chemistry of polymer solutions. Nauka, Moscow (in Russian)
Kimura S, Shiraishi N, Yanagisawa S (1975) A new thermoplastic, 1,2-polybutadiene JSR RB: properties and applications. Polym Plast Technol Eng 5:83–105
Kalinchev EL, Sakovtseva MB (1983) Properties and treatment of thermoplastics: reference manual. Khimiya, Leningrad (in Russian)
Ozawa T (1965) A new method of analyzing thermogravimetric data. Bull Chem Soc Jpn 38:1881–1886
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Glazyrin, A.B., Abdullin, M.I., Atnabaeva, E.R. et al. Synthesis and characterization of new polymers containing cyclopropane groups. Polym. Bull. 76, 3643–3657 (2019). https://doi.org/10.1007/s00289-018-2559-8
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-018-2559-8