Polyester from dimethylketene and acetaldehyde: Direct copolymerization and β-lactone ring-opening polymerization

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 49, Issue 19, 2011, Pages 4129-4138

  Brestaz, Marc ^a   Desilles, Nicolas ^a   Le, Guillaume ^a,b   Bunel, Claude ^a  

^a Normandie Université   (France)

^b ARKEMA   (France)

Author keywords

anionic polymerization; dimethylketene; polyesters; ring opening polymerization; synthesis

Indexed keywords

ALIPHATIC POLYESTER; ANIONIC COPOLYMERIZATION; CRYSTALLINITIES; DIMETHYLKETENE; DIRECT COPOLYMERIZATION; ENDOTHERMIC PEAKS; TWO-STEP PROCESS;

ACETALDEHYDE; ANIONIC POLYMERIZATION; COPOLYMERIZATION; COPOLYMERS; DIFFERENTIAL SCANNING CALORIMETRY; ESTERS; NUCLEAR MAGNETIC RESONANCE; POLYDISPERSITY; POLYESTERS; POLYMERS; RESONANCE; TOLUENE; X RAY DIFFRACTION;

RING OPENING POLYMERIZATION;

EID: 80052232096     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.24854     Document Type: Article

References (84)

1. Staudinger, H., Ber Dtsch Chem Ges 1905, 38, 1735-1739.
2. Tidwell, T. T., Ketenes; Wiley Interscience: New York, 1995.
3. Seikaly, H. R.; Tidwell, T. T., Tetrahedron 1986, 42, 2587-2613.
4. Zarras, P.; Vogl, O., Prog Polym Sci 1991, 16, 173-201.
5. Hasek, R. H., Encyclopedia of Polymer Science and Technology, 3rd ed.; Wiley: New York, 1980; Vol. 13.
6. Satchell, D. P. N.; Satchell, R. S., Chem Soc Rev 1975, 4, 231-250.
7. Hanford, W. E.; Sauer, J. C., Org React 1946, 108-140.
8. Haener, R.; Laube, T.; Seebach, D., J Am Chem Soc 1985, 107, 5396-5403.
9. Ogata, Y.; Adachi, K., J Org Chem 1982, 47, 1182-1184.
10. Harpp, D. N.; Bao, L. Q.; Black, C. J.; Gleason, J. G.; Smith, R. A., J Org Chem 1975, 40, 3420-3427.
11. Clemens, R. J., Chem Rev 1986, 86, 241-318.
12. Brady, W. T., Tetrahedron 1981, 37, 2949.
13. Hayki, N.; Desilles, N.; Burel, F., Macromol Chem Phys 2011, 112, 375-382.
14. Staudinger, H.; Felix, F.; Harder, H., Helv Chim Acta 1925, 8, 306-332.
15. Natta, G.; Mazzanti, G.; Pregaglia, G., U.S. Patent 3,350,357, 1967.
16. Natta, G.; Mazzanti, G.; Pregaglia, G.; Binaghi, M., Makromol Chem 1961, 44, 537-549.
17. Pregaglia, G.; Binaghi, M., Macromol Syn 1969, 3, 152-160.
18. Egret, H., Ph.D. Thesis, University of Rouen, Rouen, France, 1998.
19. Egret, H.; Couvercelle, J.-P.; Belleney, J.; Bunel, C., Eur Polym J 2002, 38, 1953-1961.
20. Bienvenu, A., Ph.D. Thesis, INSA of Rouen, Rouen, France, 2004.
21. Hasek, R. H.; Clark, R. D.; Elam, E. U.; Martin, J. C., J Org Chem 1962, 27, 60-64.
22. Yamashita, Y.; Nunomoto, S., Makromol Chem 1962, 58, 244-246.
23. Yamashita, Y.; Miura, S.; Nakamura, M., Makromol Chem 1963, 68, 31-47.
24. Hasek, R. A.; Elam, E.U., U.S. Patent 3,201,474, 1965.
25. Cash, G. O.; Martin, J. C., U.S. Patent 3,321,441, 1967.
26. Natta, G.; Mazzanti, G.; Pregaglia, G.; Binaghi, M., J Am Chem Soc 1960, 82, 5511-5512.
27. Natta, G.; Mazzanti, G.; Pregaglia, G.; Binaghi, M., G.B. Patent 1,015,395, 1965.
28. Natta, G.; Mazzanti, G.; Pregaglia, G.; Binaghi, M., U.S. Patent 3,337,502, 1967.
29. Natta, G.; Pregaglia, G. F.; Binaghi, M., Macromol Syn 1972, 4, 73-75.
30. Natta, G.; Mazzanti, G.; Pregaglia, G. F.; Pozzi, G., J Polym Sci 1962, 58, 1201-1210.
31. Natta, G.; Mazzanti, G.; Pregaglia, G.; Pozzi, G., G.B. Patent 950,508, 1964.
32. Miller, R. G. J.; Nield, E.; Turner-Jones, A., Chem Ind 1961, 44-46.
33. Natta, G.; Pregaglia, G.; Mazzanti, G.; Binaghi, M.; Pozzi, G.; Oddo, N.; Zamboni, V., G.B. Patent 970,018, 1964.
34. Pregaglia, G. F.; Binaghi, M., In Encyclopedia of Polymer Science and Technology, Wiley: New York, 1968; Vol. 8, pp 45-57.
35. Natta, G.; Mazzanti, G.; Pregaglia, G.; Binaghi, M.; Peraldo, M., J Am Chem Soc 1960, 82, 4742-4743.
36. Pommier, A.; Pons, J. M., Synthesis 1993, 5, 441-459.
37. Nations, R. G.; Hasek, R. H., U.S. Patent 3,221,028, 1965.
38. Steadman, T. R., U.S. Patent 2,424,589, 1947.
39. Hagemeyer, H. J., Jr., U.S. Patent 2,478,388, 1949.
40. Steadman, T. R.; Breyfogle, P. L., U.S. Patent 2,424,590, 1947.
41. Küng, F. E., U.S. Patent 2 356,459, 1944.
42. Hagemeyer, H. J., Jr., U.S. Patent 2,456,503, 1948.
43. Caldwell, J. R., U.S. Patent 2,518,662, 1950.
44. Caldwell, J. R., U.S. Patent 2,739,158, 1956.
45. Mathes, N.; Jaacks, V., Makromol Chem 1971, 142, 209-225.
46. Yamashita, Y.; Ito, K.; Nakakita, F., Makromol Chem 1969, 127, 292-295.
47. Kricheldorf, H. R.; Garaleh, M.; Schwarz, G., J Macromol Sci Pure Appl Chem 2005, A42, 139-148.
48. Kricheldorf, H. R.; Jonte, J. M.; Dunsing, R., Makromol Chem 1986, 187, 771-785.
49. Gresham, T. L.; Jansen, J. E.; Shaver, F. W.; Bankert, R. A.; Fiedorek, F. T., J Am Chem Soc 1951, 73, 3168-3171.
50. Kricheldorf, H. R.; Scharnagl, N.; Jedlinski, Z., Polymer 1996, 37, 1405-1411.
51. Kricheldorf, H. R.; Berl, M.; Scharnagl, N., Macromolecules 1988, 21, 286-293.
52. Kurcok, P.; Kowalczuk, M.; Hennek, K.; Jedlinski, Z., Macromolecules 1992, 25, 2017-2020.
53. Kurcok, P.; Matuszowicz, A.; Jedlinski, Z.; Kricheldorf, H. R.; Dubois, P.; Jerome, R., Macromol Rapid Commun 1995, 16, 513-519.
54. Jedlinski, Z.; Kowalczuk, M.; Kurcok, P., Macromolecules 1991, 24, 1218-1219.
55. Jedlinski, Z.; Kurcok, P.; Kowalczuk, M., Macromolecules 1985, 18, 2679-2683.
56. Moller, M.; Kange, R.; Hedrick, J. L., J Polym Sci Part A: Polym Chem 2000, 38, 2067-2074.
57. Vivas, M.; Mejias, N.; Contreras, J., Polym Int 2003, 52, 1005-1009.
58. Jaipuri, F. A.; Bower, B. D.; Pohl, N. L., Tetrahedron: Asymmetry 2003, 14, 3249-3252.
59. Kricheldorf, H. R.; Kreiser-Saunders, I.; Scharnag, N., Makromol Chem Macromol Symp 1990, 32, 285-298.
60. Kricheldorf, H. R.; Eggerstedt, S., Macromolecules 1997, 30, 5693-5697.
61. Kricheldorf, H. R.; Lee, S.-R.; Scharnagl, N., Macromolecules 1994, 27, 3139-3146.
62. Jedlinski, Z.; Kurcok, P.; Kowalczuk, M.; Kasperczyk, J., Makromol Chem 1986, 187, 1651-1656.
63. Kricheldorf, H. R.; Scharnagl, N., J Macromol Sci Chem 1989, A26, 951-968.
64. Wilson, D. R.; Beaman, R. G., J Polym Sci Part A-1: Polym Chem 1970, 8, 2161-2170.
65. Jedlinski, Z.; Kurcok, P.; Kowalczuk, M.; Matuszowicz, A.; Dubois, P.; Jerome, R.; Kricheldorf, H. R., Macromolecules 1995, 28, 7276-7280.
66. Teranishi, K.; Araki, T.; Tani, H., Macromolecules 1972, 5, 660-661.
67. Teranishi, K.; Iida, M.; Araki, T.; Yamashita, S.; Tani, H., Macromolecules 1974, 7, 421-427.
68. Iida, M.; Araki, T.; Teranishi, K.; Tani, H., Macromolecules 1977, 10, 275-284.
69. Ramiandrasoa, P.; Guerin, P.; Girault, J. P.; Bascou, P.; Hammouda, A.; Cammas, S.; Vert, M., Polym Bull 1993, 30, 501-508.
70. Etienne, Y.; Fischer, N., Fr Patent 1,231,163, 1960.
71. Ames, W. A.; Ward, J. J.; Carter, E. H. J., U.S. Patent 3,879,352, 1975.
72. Bigdeli, E.; Lenz, R. W., Macromolecules 1978, 11, 493-496.
73. Rieth, L. R.; Moore, D. R.; Lobkovsky, E. B.; Coates, G. W., J Am Chem Soc 2002, 124, 15239-15248.
74. Guillaume, C.; Carpentier, J.-F.; Guillaume, S. M., Polymer 2009, 50, 5909-5917.
75. Barbaud, C.; Abdillah, F.; Fabienne, F.; Guerrouache, M.; Guerin, P., Des Monomers Polym 2003, 6, 353-367.
76. Barbaud, C.; Fay, F.; Abdillah, F.; Randriamahefa, S.; Guerin, P., Macromol Chem Phys 2004, 205, 199-207.
77. Moyano, A.; Pericas, M. A.; Valenti, E., J Org Chem 1989, 54, 573-582.
78. Jackson, M. S.; Wild, M. S.; Varley, J. H., G.B. Patent 2,115,432, 1983.
79. Van Duuren, B. L.; Langseth, L.; Goldschmidt, B. M.; Orris, L., J Natl Cancer Inst 1967, 39, 1217-1228.
80. Salkowski, H., Jr,. J Prakt Chem 1923, 106, 253-265.
81. Pregaglia, G. F.; Binaghi, M., Macromol Syn 1968, 3, 152-160.
82. Stanin, T. E.; Brown, V. L., Jr., Fr Patent 1,381,831, 1964.
83. Mugno, M.; Bornengo, M., Chimica e l'Industria 1964, 46, 5-9.
84. McConnell, W. V.; Moore, W. H., J Org Chem 1963, 28, 822-827.