Synthesis and Characterization of Copolymers from Hindered Amines and Vinyl Monomers
Chinelatto, M. A.; Agnelli, José Augusto M.; Canevarolo, Sebastião V.
http://dx.doi.org/10.4322/polimeros.2014.046
Polímeros: Ciência e Tecnologia, vol.24, n1, p.30-36, 2014
PlumX Metrics
- Citations
- Citation Indexes: 7
- Patent Family Citations: 1
- Usage
- Full Text Views: 6653
- Abstract Views: 518
- Captures
- Readers: 18
- Mentions
- References: 1
Downloads: 0
Views: 1738
Abstract
New copolymers from hindered amines and vinyl monomers were synthesized by radical chain polymerization. To obtain polymeric HALS, acrylamide-(1ATP) and acrylate-(4ATP) monomers, derivatives from 2,2,6,6-tetramethylpiperidine and 2,2,6,6-tetramethyl-4-piperidinol were synthesized. The radical chain polymerization of 1ATP with styrene (Sty) using 1-butanethiol (BTN) resulted in a copolymer with 95 units of Sty and 15 units of 1ATP. The radical chain polymerization of 1ATP and vinyl acetate (VAc) has produced only 1ATP homopolymer. In the chain polymerization of 4ATP with Sty or VAc, the hydrogen atom bonded to the nitrogen of 4ATP is labile enough to originate another radical at this site. The steric hindrance imposed by methyl groups on this bonding site hampers its reaction with other propagating species and the formation of a copolymer or network structure will be dependent on the size of the pendent group in the vinyl monomer.
Keywords
Degradation, hindered amine, photooxidation, polymeric HALS, stabilizers, synthesis
References
1. Andrady, A. L.; Hamid, S. H.; Hu, X. & Torikai, A. – J. Photochem. Photobiol. B: Biol., 46, p.96 (1988). http:// dx.doi.org/10.1016/S1011-1344(98)00188-2
2. Feldman, D. – J. Polym. Environ., 10, p.163 (2002). http:// dx.doi.org/10.1023/A:1021148205366
3. Rabek, J. F. – “Polymer Photodegradation: Mechanisms and Experimental Methods”, Chapman & Hall, London (1995).
4. Ammala, A.; Bateman, S.; Dean, K.; Petinakis, E.; Sangwan, P.; Wong, S.; Yuan, Q.; Yu, L.; Patrick, C. & Leong, K. H. – Prog. Polym. Sci., 36, p.1015 (2011). http:// dx.doi.org/10.1016/j.progpolymsci.2010.12.002
5. Pilař, J.; Michálková, D.; Šedĕnková, I.; Pfleger, J. & Pospíšil, J. – Polym. Degrad. Stab., 96, p.847 (2011). http:// dx.doi.org/10.1016/j.polymdegradstab.2011.02.004
6. Rossi, I.; Venturini, A. & Zedda, A. – J. Am. Chem. Soc., 121, 7914 (1999). http://dx.doi.org/10.1021/ ja9906655
7. BilIingham, N. C. & Calvert, P. D. – “The Degradation and Stabilisation of Polyolefins – An Introduction”, in: Degradation and Stabilisation of Polyolefins, cap. 1, Norman S. Allen (ed), Applied Science, London (1983).
8. Carlsson, D. J. & Wiles, D. M. – J. Macromol. Sci. C: Polym. Rev., 14, p.65 (1976). http://dx.doi. org/10.1080/15321797608076113
9. Delprat, P.; Duteurtre, X. & Gardette, J. L. – Polym. Degrad. Stab., 50, p.1 (1995). http://dx.doi.org/10.1016/0141- 3910(95)00061-P
10. Philippart, J. L.; Posada, F. & Gardette, J. L. – Polym. Degrad. Stab., 49, p.285 (1995). http://dx.doi. org/10.1016/0141-3910(95)87010-5
11. Gugumus, F. – Polym. Degrad. Stab., 40, p.167 (1993). http://dx.doi.org/10.1016/0141-3910(93)90208-Z
12. Gijsman, P. – Polym., 43, p.1573 (2002). http://dx.doi. org/10.1016/S0032-3861(01)00708-X
13. Gugumus, F. – Die Angew. Makromol. Chem., 176, p.241 (1990). http://dx.doi.org/10.1002/apmc.1990.051760121
14. Gugumus, F. – Polym. Degrad. Stab., 39, p.117-135 (1993). http://dx.doi.org/10.1016/0141-3910(93)90131-2
15. Minagawa, M. – Polym. Degrad. Stab., 25, p.121-141 (1989). http://dx.doi.org/10.1016/S0141-3910(89)81004-3
16. Smoliak, L. Y. & Prokopchuk, N. R. – Polym. Degrad. Stab., 82, p.169 (2003). http://dx.doi.org/10.1016/S0141- 3910(03)00180-0
17. Malík, J.; Hrivík, A. & Alexyová, D. – Polym. Degrad. Stab., 35, p.125 (1992). http://dx.doi.org/10.1016/0141- 3910(92)90103-C
18. Xue, B. & Toyota, A. – Polym. Bull., 62, p.327 (2009). http://dx.doi.org/10.1007/s00289-008-0028-5
19. Sun, G. J.; Jang, H. J.; Kaang, S. & Chae, K. H. – Polym., 43, p.5855 (2002). http://dx.doi.org/10.1016/ S0032-3861(02)00514-1
20. Singh, R. P.; Patwa, A. N.; Desai, S. M.; Pandey, J. K.; Solanky, S. S. & Prasad, A. V. – J. Appl. Polym. Sci., 90, p.1126 (2003). http://dx.doi.org/10.1002/app.12672
21. Pan, J.; Cheng, W.; Song, Y. & Hu, X. – Polym. Degrad. Stab., 39, p.85 (1993). http://dx.doi.org/10.1016/0141- 3910(93)90128-6
22. Pan, J. Q. – Chin. J. Polym. Sci., 19, p.341 (2001).
23. Al-Malaika, S.; Ibrahim, A. Q. & Scott, G. – Polym. Degrad. Stab., 22, p.233 (1988). http://dx.doi.org/10.1016/0141- 3910(88)90013-4
24. Al-Malaika, S.; Scott, G. & Wirjosentono, B. – Polym. Degrad. Stab., 40, p.233 (1993). http://dx.doi. org/10.1016/0141-3910(93)90210-A
25. Odian, G. – “Principles of Polymerization”, John Wiley, New Jersey (2004).
