On the importance of the amide-bonded hydrogen atom in the cationically induced oligomerization of Af-vinylamides

Macromolecules

Volumn 33, Issue 15, 2000, Pages 5325-5335

  Madl, A ^a   Spange, S ^a  

^a CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CATIONIC POLYMERIZATION; HYDROGEN BONDS; INITIATORS (CHEMICAL); MOLECULAR STRUCTURE; POLYAMIDES; PROTONS; REACTION KINETICS; VINYL RESINS;

DIMERIZATION; OLIGOMERIZATION;

OLIGOMERS;

EID: 0034224403     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9920285     Document Type: Article

References (45)

1. a) Dawson, D. J.; Gless, R. D.; Wingard, E. W., Jr. J. Am. Chem. Soc. 1976, 98, 5996-6000.
2. (b) Badesso, R. J.; Nordquist, A. F.; Pinschmidt, R. K., Jr.; Sagl, D. J. Adv. Chem. Ser. 1996, 248, 489-504.
3. a) Kirsh, Y. E.; Berestova, S. S.; Aksenov, A. I.; Karaputadze, . T. M. RUSS. J. Phys. Chem. 1990, 64,1894-1898;
4. (b) Nagata, M.; Yoshikawa, O.; Sakai, M.; Sakakibara, Y.; Uchino, N. Nippon Kagaku Kaishi 1975, 10, 1819-1822
5. [Chem. Abstr. 1976, 84, 5731].
6. Pinschmidt, R. K., Jr.; Sagl, D. J. In Polymeric Materials Encyclopedia; Salamone, J. C. Ed.; CRC Press: New York, 1996; Vol. 9/P, p 7095.
7. Barabas, E. S. In Encyclopedia of Polymer Science and Engineering; Mark, H. F., Bikales, N. M., Overberger, C. G., Menges, G., Kroschwitz, J. I., Eds.; John Wiley & Sons: New York, 1989; Vol. 17, p 199ff.
8. DE 19,642,490 Al (1996). Inventors: Breitenbach, J.; Schade, C.; Sigwart, C.; Müller, U.; Hesse, M.; Negele, A.; Rübenacker, M.; Eller, K, assigned to BASF AG [Chem. Abstr. 1998, 128, 270985].
9. US patent 2,231,905 (1941); Inventors: Hanford, W. E.; Stevenson, H. B., assigned to duPont [Chem. Abstr. 1941,35, 3267].
10. Ben-Ishai, D.; Giger, R. Tetrahedron Lett. 1965, SO, 45234526.
11. a) US patent 5,280,077 (1994). Inventors: Carroll, W. E.; Pinschmidt, R. U., Jr., assigned to Air Products Chemicals [Chem. Abstr. 1994, 120, 299557].
12. (b) DE 44 03519 (1994). Inventors: Kobayashi, S.; Uyama, H.; Sawayama, S.; Satoh, K., assigned to Mitsubishi Kasai Corp. [Chem. Abstr. 1995, 122, 56829].
13. US patent 5,373,076 (1994) Inventors: Pinschmidt, R. U., Jr.; Carroll, W. E., assigned to Air Products Chemicals [Chem. Abstr. 1995, 122, 315375].
14. Pinschmidt, R. K, Jr.; Wasowski, L. A.; Orphanides, G. G.; Yacoub, K Prog. Org. Coatings 1996, 27, 209-218.
15. Pinschmidt, R. K., Jr.; Renz, W. L.; Carroll, W. E.; Yacoub, K.; Drescher, J.; Nordquist, A. F.; Chen, N. J. Macromol. Sci.-Pure Appl. Chem. 1997, A34, 1885-1905.
16. a) Spange, S.; Madl, A.; Eismann, U.; Utecht, J. Macromol. Rapid Commun. 1997,18,1075-1083.
17. (b) Madl, A.; Spange, S.; Waldbach, T.; Anders, E.; Mahr, N. Macromol. Chem. Phys. 1999,2000,1495-1505.
18. Madl, A.; Spange, S.; Mahr, N. Polym. Bull. 2000, 44, 39-46.
19. DE 2919755 (1979). Inventors: Jensen, H.; Schmidt, E.; Mitzlaff, M.; Cramer, J.; Pistorius, R.; Pietsch, H.; Dehmer, C., assigned to Hoechst AG [Chem. Abstr. 1981,94,174381].
20. Product information NVF, Mitsubishi Kasai.
21. a) Homer, A. B.; Johnson, C. D. In The Chemistry of Amides; Zabicky, J., Ed.; Interscience Publishers: London, 1970; p 188ff.
22. (b) Cho, S. J.; Cui, C.; Lee, J. Y.; Park, J. K.; Suh, S. B.; Park, J.; Kim, B. H.; Kim, K. S. J. Org. Chem. 1997; 62, 4068-4071.
23. Lin, H.-Y.; Ridge, D. P.; Uggerud, E.; Vulpius, T. J. Am. Chem. Soc. 1994,116, 2996-3004.
24. Antonczak, S.; Ruiz-Löpez, M. F.; Rivail, J.-L. J. Am. Chem. Soc. 1997, 116 33912-3921
25. US'5,373,076 (ref 6c). See example 8, polymerization of VFA (neat) with trifluoroacetic anhydride: 3.59 g of VFA feed, 2.3 g of crude OVFA (64%), and 1.6 g of OVFA after reprecipitation (45%)
26. Madl, A.; Spange, S. Macromol. Symp. 2000, in press.
27. Madl, A. Master of Chemistry Thesis, 1996, Chemnitz University of Technology.
28. Heublein, G.; Heibig, M. J. Prakt. Chem. 1972, 314, 1-14.
29. (a) See ref 15.
30. (b) Spange, S.; Meyer, T. Macromol Chem. Phys. 1999, 200, 1655-1661.
31. Murano, M.; Harwood, H. J. Macromolecules 1970, 3, 605609.
32. Sawamoto, M.; Fujimori, J.; Higashimura, T. Macromolecules 1987, 20, 916-920.
33. DE 4030380 Al (1990). Inventors: Fikentscher, R.; Kröner, M., assigned to BASF AG [Chem. Abstr. 1992, 117, 49443].
34. Lasne, M.-C.; Ripoll, J.-L.; Thuillier, A. J. Chem. Res., Synop. 1982, 214-215.
35. (a) Gandini, A.; Cheredame, H. Adv. Polym. Sei. 1980, 341 35, 81.
36. (b) Giusti, P.; Andruzzi, F. Makromol. Chem. 1966, 98, 170-178.
37. Hoffmann, H. M. R. Angew. Chem. 1969, 81, 597-618.
38. Borzilleri, R. M.; Weinreb, S. M. Synthesis 1995, 347-360.
39. (a) Beckmann, A.; Fröhlich, R.; Würthwein, E.-U. Tetrahedron Lett. 1997, 38, 5481-5484.
40. (b) Aust, N. C.; Fröhlich, R.; Hecht, J. W.; Würthwein, E.-U. Liebigs Ann. /Red. 1997, 1593-1602.
41. B3LYP/6-31+G*//B3LYP/6-31+G* ab initio calculations, performed by Würthwein, E.-U. Unpublished results, 2000, communicated to the authors.
42. (a) BASF Aktiengesellschaft, Ludwigshafen. Unpublished results, communicated to the authors, (b) Madl, A.; Spange, S. Unpublished results, 1999.
43. (a) Higashimura, T.; Miyamoto, M.; Sawamoto, M. Macromolecules 1985, 18, 611-616.
44. (b) Van Meirvenne, D.; Haucourt, N.; Goethals, E. J. Polym. Bull. 1990,23,185-190.
45. Nuyken, O.; Rie, G. Macromol. Rep. 1995, A32, 25-38.