Definition
In polymer chemistry, ring-opening polymerization is a form of chain-growth polymerization during which the terminal end of the polymer acts as the reactive center for the addition of cyclic monomers to increase the length of the polymer via ionic propagation. The treatment of certain cyclic compounds with a catalyst causes ring cleavage, which is followed by polymerization to afford high-molecular-weight polymers. When the reactive center of the propagating chain is a carbocation in the transition state, the polymerization is denoted cationic ring-opening polymerization. Exemplary cyclic monomers polymerized by this method include the following:
- 1.
Cyclic ethers
- 2.
Cyclic esters (lactones)
- 3.
Cyclic acetals
- 4.
Cyclic amides (lactams)
- 5.
Cyclic amines
- 6.
Cyclic sulfides
- 7.
Cyclic imino ethers
Cyclic Ethers
Propagation during cationic polymerization of cyclic ethers is generally considered to proceed via a tertiary oxonium ion. A variety of initiators, similar to those used...
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Inoue S, Aida T (1984) Cyclic ethers, Chapter 4. In: Ivin J, Saegusa T (eds) Ring-opening polymerization, vol 1. Elsevier, London
Penczek S, Kubisa P (1989) Cationic ring-opening polymerization: ethers, Chapter 48. In: Eastmond GC, Ledwith A, Russo S, Sigwalt P (eds) Comprehensive polymer science, vol 3. Pergamon Press, London
Kricherdorf HR, Jonte JM, Dunsing R (1986) Polylactones, 7. The mechanism of cationic polymerization of β-propiolactone and ε-caprolactone. Makromol Chem 187:771–785. doi:10.1002/macp.1986.021870408
Peczek S, Slomkowski S (1989) Cationic ring-opening polymerization: cyclic ethers, Chapter 50. In: Eastmond GC, Ledwith A, Russo S, Sigwalt P (eds) Comprehensive polymer science, vol 3. Pergamon Press, London
Kawakami Y, Yamashita Y (1977) Macrocyclic formals. 3. Two-stage polymerization of 1,3-dioxacycloalkanes. Macromolecules 10:837–839. doi:10.1021/ma60058a022
Matyjaszewski K, Zielinski M, Kubisa P, Slomkowski S, Chojnowski J, Penczek S (1980) Kinetically controlled formation of macrocyclic oligomers in the ring-opening polymerization. Makromol Chem 181:1469–1482. doi:10.1002/macp.1980.021810710
Okada M, Hisada T, Sumitomo H (1978) Cationic polymerization of methyl substituted 1,3-dioxepanes. Makromol Chem 179:959–967. doi:10.1002/macp.1978.021790410
Kawakami Y, Yamashita Y (1979) Macrocyclic formals. 7. The nature of the growing species in the cationic polymerization of 1,3,6,9-tetraoxacycloundecane. Macromolecules 12:399–403. doi:10.1021/ma60069a009
Okada M, Hirasawa T, Sumitomo H (1989) Polymerization of bicyclic acetals, 18. Propagation processes in the cationic ring-opening polymerization of 6,8-dioxabicyclo[3.2.1]octane derivatives having a 3(e)-benzyloxy group as a common substituent. Makromol Chem 190:1289–1301. doi:10.1002/macp.1989.021900609
Sumitomo H, Okada M (1984) Sugar anhydrides and related bicyclic acetals, Chapter 5. In: Ivin J, Saegusa T (eds) Ring-opening polymerization, vol 1. Elsevier, London
Sebenda J (1988) Cationic polymerization and copolymerization of lactams and lactam derivatives. Makromol Chem Macromol Symp 13(14):97–110. doi:10.1002/masy.19880130109
Tomalia DA, Killat GR (1985) Alkyleneimine polymers. In: Mark HF, Bikales NM, Overberger CG, Menges G (eds) Encyclopedia of polymer science and engineering, vol 1, 2nd edn. Wiley-Interscience, New York, pp 680–739
Aida T, Kawaguchi K, Inoue S (1990) Zinc N-substituted porphyrins as novel initiators for the living and immortal polymerizations of episulfide. Macromolecules 23:3887–3892. doi:10.1021/ma00219a004
Kobayashi S, Saegusa T (1984) Ring-opening polymerization, vol 2. Elsevier Applied Science, Essex, Chapter 11
Kobayashi S, Uyama H, Narita Y (1990) Novel bifunctional initiator for polymerization of 2-oxazolines via fast initiation. Macromolecules 23:353–354. doi:10.1021/ma00203a062
Dworak A, Schulz CR (1991) Star polymers and block copolymers of 2-oxazolines using chloroformates as initiators. Makromol Chem 192:437–445. doi:10.1002/macp.1991.021920223
Hrkach SJ, Matyjaszewski K (1992) Reaction of 2-methyl-2-oxazoline with trimethylsilyl initiators: an unusual mode of ring opening. Macromolecules 25:2070–2075. doi:10.1021/ma00034a002
Saegusa T, Ikeda H, Fujii H (1973) Isomerization polymerization of 2-oxazoline. V. Kinetic studies on the polymerization of 2-oxazoline. Macromolecules 6:315–319. doi:10.1021/ma60033a002
Saegusa T, Ikeda H, Fujii H (1973) Isomerization polymerization of 2-oxazoline. III. Reactivities of unsubstituted and 2-substituted 2-oxazoline monomers. Polym J 4:87–92. doi:10.1295/polymj.4.87
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer-Verlag Berlin Heidelberg
About this entry
Cite this entry
Takasu, A., Hayashi, T. (2015). Cationic Ring-Opening Polymerization. In: Kobayashi, S., Müllen, K. (eds) Encyclopedia of Polymeric Nanomaterials. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-29648-2_176
Download citation
DOI: https://doi.org/10.1007/978-3-642-29648-2_176
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-29647-5
Online ISBN: 978-3-642-29648-2
eBook Packages: Chemistry and Materials ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics