Improved synthesis of 2-vinyl-4,5-dicyanoimidazole and characterization of its polymers

Macromolecules

Volumn 33, Issue 23, 2000, Pages 8597-8603

  Johnson, David M ^a,b   Rasmussen, Paul G ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b The University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; MOLECULAR WEIGHT; NITROGEN COMPOUNDS; OLIGOMERS; SYNTHESIS (CHEMICAL); TITRATION;

MARK-HOUWINK CONSTANTS; POLYDISPERSITY; POLYVINAZENE;

ORGANIC POLYMERS;

EID: 0034315898     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma000779x     Document Type: Article

References (20)

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4. Rasmussen, P. G.; Reybuck, S. E.; Jang, T.; Lawton, R. G. Diaminomaleonitrile Derivative Compounds, Polymers, and Method of Producing Same. US Patent 5,712,408, 1998; Chem. Abstr. 1998, 128, 128380c.
5. Rasmussen, P. G.; Reybuck, S. E.; Jang, T.; Lawton, R. G. Diaminomaleonitrile Derivative Compounds, Polymers, and Method of Producing Same. US Patent 5,712,408, 1998; Chem. Abstr. 1998, 128, 128380c.
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9. Hosogai, T. Preparation Method of 2-Substituted 4,5-Dicyanoimidazoles. Jpn. Kokai Tokkyo Koho, SHO 49-134676, 1983; Chem. Abstr. 1975, 82, 170924g.
10. Rasmussen, P. G.; Reybuck, S. E.; Johnson, D. M.; Lawton, R. G. Cyclic imidazole compounds having relatively low hydrogen content and relatively high nitrogen content and polymers formed therefrom. U.S. Patent 6096899, 2000.
11. Odian, G. Principles of Polymerization, 3rd ed.; John Wiley and Sons: New York, 1991.
12. The kinetic analysis routine of the NMR spectrometer used for this experiment did not have a routine established to measure integral intensity. However, the peak shapes for the relevant signals are doublets of doublets, yielding four equal height peaks, whose height should be proportional to integral area and hence appropriate for kinetic analysis.
13. (a) Barni, E.; Bianchi, R.; Gervasio, G.; Peters, A. T.; Viscardi, G. Structural Characterization of 4-Cyanoimidazolium-5-olate, 4,4-Diphenyl-5-imidazolinone, and 4,5-Dicyanoimidazole. A Novel Mesoionic Compound and Decoding of Intermolecular Hydrogen Bonds. J. Org. Chem. 1997, 62, 7037-7043. The infrared spectra of the crystals described in (a) and (b) show the presence or absence of a characteristic signature for the 1,3-H bonded imidazole chains.
14. We are grateful to Larry Markowski, of the Beckmann Institute, University of Illinois, Urbana, IL, for obtaining light-scattering GPC data for our compounds in NMP.
15. (a) Morowetz, H. Macromolecules in Solution; Interscience Publishers: New York, 1965; pp 348-356.
16. (b) Green, M. M.; Schultz, G.; Jha, S. K.; Morawetz, H. The Chiral Properties of a Water Soluble Reversible pH Dependent Supramolecular Complex Between an Atropisomerically Labeled Poly(methacrylic acid) and a Cyclodextrin. ACS Polym. Prepr. 1996, 37, 505.
17. Modified from: (a) Reybuck, S. E.; Rasmussen, P. G.; Jang, T.; Lawton, R. G. Synthesis of Conjugated Mono-Anil Derivatives and Their Polymers Formed by Thermolysis. Polym. Prepr. 1997, 38 (1), 151-2.
18. (b) Reybuck, S. E. Synthesis and Characterization of Mono-anil Derivatives of Diaminomaleonitrile and Vinylic Monomers and Polymers from 4,5-dicyano-2-vinylimidazoles. B.S. Thesis, University of Michigan, 1997.
19. Modified from ref 6.
20. Modified from: Sorenson, W. R.; Campbell, T. W. Preparative Methods of Polymer Chemistry; Interscience Publishers: New York, 1961.