Hydrogen-Transfer Polymerization of Vinyl Monomers Derived from 4-Methylbenzoyl Isocyanate and Acrylamide Derivatives

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 37, Issue 4, 1999, Pages 465-472

  Iwamura, Takeru ^a   Tomita, Ikuyoshi ^a   Suzuki, Masato ^a   Endo, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Acrylamide; Benzoyl isocyanate; Hydrogen transfer polymerization

Indexed keywords

ACRYLIC MONOMERS; CHARGE TRANSFER; ORGANIC SOLVENTS; ORGANOMETALLICS; PROTONS;

PROTON TRANSFER POLYMERIZATION;

ANIONIC POLYMERIZATION;

EID: 0033078365     PISSN: 0887624X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0518(19990215)37:4<465::AID-POLA10>3.0.CO;2-3     Document Type: Article

References (21)

1. German Patent 316, 902, 1915.
2. Arcus, C. L.; Prydal, B. S. J Chem Soc 1957, 1091.
3. Billeter, O. C. Ber 1903, 36, 3213.
4. Endo, T.; Kanamaru, M.; Takata, T. Macromolecules 1994, 27, 3694.
5. Kanamaru, M.; Takata, T.; Endo, T. Macromolecules 1994, 27, 7492.
6. Kanamaru, M.; Takata, T.; Endo, T. J Polym Sci, Part A: Polym Chem 1995, 33, 1361.
7. Kanamaru, M.; Takata, T.; Endo, T. Macromolecules 1995, 28, 7979.
8. Kanamaru, M.; Takata, T.; Endo, T. Macromol Chem Phys 1996, 197, 1795.
9. Iwamura, T.; Tomita, I.; Suzuki, M.; Endo, T. J Polym Sci, Part A: Polym Chem 1998, 36, 1515.
10. Iwamura, T.; Tomita, I.; Suzuki, M.; Endo, T. J Polym Sci, Part A: Polym Chem 1998, 36, 1491.
11. (b) Iwamura, T.; Tomita, I.; Suzuki, M.; Endo, T. Bull Chem Soc Jpn 1998, 71, 1137.
12. Breslow, D. S.; Hulse, G. E.; Matlack, A. S. J Am Chem Soc 1957, 79, 3760.
13. Okamura, S.; Oishi, Y.; Higashimura, T.; Senoo, T. Koubunshi Kagaku 1962, 19, 323.
14. Wexler, H. Makromol Chem 1968, 115, 262.
15. Tsunetsugu, T.; Matsuo, T.; Furukawa, J. Makromol Chem 1967, 107, 222.
16. Guita, M.; Camino, G.; Trossarelli, L. Makromol Chem 1970, 131, 309.
17. Speziale, A. J.; Smith, L. R. J Org Chem 1963, 28, 1805.
18. 2= CHCONHCONHTs) proceeds via the latter path (i.e., the elimination of N-H), which might be also plausible as the initiation step of the polymerization of 1, as shown in Scheme 5.
19. 1H-NMR spectra actually indicated the existence of the end-acryloyl moieties, the content was lower than expected. This might be due to the reactions such as the nucleophilic attack of the growing N-anions to the terminal acryl group and any intermolecular cyclization processes.
20. The possibility of the branched structures in the polymer cannot be denied because N-anions might be also generated in the repeating units of the polymer from which grafting reactions may occur.
21. By means of the elimination process, the polymer might be contaminated with other imide structural units as shown in Scheme 4. Because of the structural resemblance of these units to the hydrogen-transfer units (the x and/or y units), they might be also characterized as the x and/or y units by spectroscopic methods.