Abstract
In this work we report the synthesis and characterization of a new series of spiropolymers which are a subclass of ladder polymers. For the synthesis of spiropolymers, multihydroxy functional monomers have been synthesized and allowed to react with 1,4 cyclohexanedicarbaldehyde in the presence of an acid catalyst to give new polyspiroacetals. In order to understand polymer structure, model compounds of each polymer were synthesized and characterized. The effects of different multihydroxy monomers on the properties of the resulting polymers have been examined. The polymers were characterized by Fourier transform infrared spectroscopy (FTIR), solid-state 13C nuclear magnetic resonance (NMR), termogravimetric analysis (TGA) and differential scanning calorimetry (DSC) methods. The spiropolymers are thermally stable and have a high degree of chemical stability. They are completely soluble in hexafluoroisopropanol (HFIP) and can be recovered from this solvent.
Similar content being viewed by others
References
Cohen SM, Lavin E (1962) J Appl Polym Sci 23:503–507
Cohen SM, Hunt CF, Kass RE, Markhart AH (1962) J Appl Polym Sci 23:508–517
Bailey WJ, Volpe AA (1970) J Polym Sci 8:2109–2122
Bailey WJ, Beam CF, Cappuccilli ED Jr, Haddad I, Volpe AA (1982) ACS Symp Ser 195:391–402
Lee K, Kim HM, Rhee JM (1991) Macromol Chem Phys 192:1033–1040
Abdel-Razık HH (2010) Turk J Chem 34:27–33
Sonmez HB, Wudl F (2003) Am Chem Soc Polym Prep 45:801–802
Sonmez HB, Kuloglu FG, Karadag K, Wudl F (2012) Polym J 44:217–223
Mannich C, Brose W (1923) Ber 566:833
Witcoff H (1951) Organic Synth Coll 4:907
Ray GC (1950) US patent 2.500.570. Chem Abstr 34:5385
Feuerbacher N, Vogtle F, Windscheidt J, Poetsch E, Nieger M (1999) Synthesis 1:117
Herwig W, Sommer S, Erbes K Farbwerke Hoechst A-G, Ger, 1.173.449
The X-ray intensity data were measured on a APEX II QUAZAR system equipped with a multilayer monochromator and a MoKα ImuS (λ = 0.71073 Å). Crystal data of model: C23H36O5. Monoclinic a = 17.5277(5) Å, α = 90°, b = 5.8292(2) Å β = 99.1620(10)°, c = 21.0112(5) Å γ = 90°, cell volume 2119.38(11) Å3, Z = 4
Acknowledgments
The authors would like to thank the crystallographer Dr. Fatma Yuksel (GIT)
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
CCDC- 910643 contain the supplementary crystallographic data for compound Model 3. This data can be obtained the supplementary file for this paper and free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
ESM 1
(PDF 95 kb)
10965_2013_97_MOESM2_ESM.cif
(CIF 15 kb)
Rights and permissions
About this article
Cite this article
Akbulut, G., Sonmez, H.B. & Wudl, F. Synthesis, characterization and properties of novel polyspiroacetals. J Polym Res 20, 97 (2013). https://doi.org/10.1007/s10965-013-0097-5
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s10965-013-0097-5