Precision vinyl acetate/ethylene (VAE) copolymers by ROMP of acetoxy-substituted cyclic alkenes

Macromolecules

Volumn 46, Issue 7, 2013, Pages 2535-2543

  Zhang, Jihua ^a   Matta, Megan E ^a   Martinez, Henry ^a   Hillmyer, Marc A ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEGREE OF CRYSTALLINITY; MECHANICAL CHARACTERIZATIONS; OPTICALLY ACTIVE; RADICAL COPOLYMERIZATION; REGIOREGULARITY; RING OPENING METATHESIS POLYMERIZATION; SEMICRYSTALLINES; WIDE ANGLE X-RAY SCATTERING;

CARBON; COPOLYMERS; DIFFERENTIAL SCANNING CALORIMETRY; HYDROGENATION; MECHANICAL PROPERTIES; POLYMERS; RING OPENING POLYMERIZATION;

POLYVINYL ACETATES;

EID: 84875999220     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma400092z     Document Type: Article

References (101)

1. Webster, O. W. Science 1991, 251, 887-893
2. Matyjaszewski, K. Prog. Polym. Sci. 2005, 30, 858-875
3. Hadjichristidis, N.; Iatrou, H.; Pitsikalis, M.; Mays, J. Prog. Polym. Sci. 2006, 31, 1068-1132
4. Ouchi, M.; Terashima, T.; Sawamoto, M. Acc. Chem. Res. 2008, 41, 1120-1132
5. Ouchi, M.; Terashima, T.; Sawamoto, M. Chem. Rev. 2009, 109, 4963-5050
6. Lutz, J. F.; Pakula, T.; Matyjaszewski, K. ACS Symp. Ser. 2003, 854, 268-282
7. Badi, N.; Lutz, J. F. Chem. Soc. Rev. 2009, 38, 3383-3390
8. Lutz, J. F. Polym. Chem. 2010, 1, 55-62
9. Hartmann, L. Macromol. Chem. Phys. 2011, 212, 8-13
10. Wu, Z.; Grubbs, R. H. J. Mol. Catal. 1994, 90, 39-42
11. Wu, Z.; Grubbs, R. H. Macromolecules 1995, 28, 3502-3508
12. Yokota, K. Prog. Polym. Sci. 1999, 24, 517-563
13. Cho, I. Prog. Polym. Sci. 2000, 25, 1043-1087
14. Cho, I. Macromol. Symp. 2003, 195, 89-94
15. Song, A. R.; Lee, J. C.; Parker, K. A.; Sampson, N. S. J. Am. Chem. Soc. 2010, 132, 10513-10520
16. Berda, E. B.; Baughman, T. W.; Wagener, K. B. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 4981-4989
17. Rojas, G.; Berda, E. B.; Wagener, K. B. Polymer 2008, 49, 2985-2995
18. Li, Z. L.; Li, L.; Deng, X. X.; Zhang, L. J.; Dong, B. T.; Du, F. S.; Li, Z. C. Macromolecules 2012, 45, 4590-4598
19. Park, H.; Choi, T.-L. J. Am. Chem. Soc. 2012, 134, 7270-7273
20. Tsarevsky, N. V.; Sumerlin, B. S.; Matyjaszewski, K. Macromolecules 2005, 38, 3558-3561
21. Lutz, J. F. Angew. Chem., Int. Ed. 2007, 46, 1018-1025
22. Takizawa, K.; Tang, C.; Hawker, C. J. J. Am. Chem. Soc. 2008, 130, 1718-1726
23. Takizawa, K.; Nulwala, H.; Hu, J.; Yoshinaga, K.; Hawker, C. J. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 5977-5990
24. Yu, T. B.; Bai, J. Z.; Guan, Z. B. Angew. Chem., Int. Ed. 2009, 48, 1097-1101
25. Berthet, M. A.; Zarafshani, Z.; Pfeifer, S.; Lutz, J. F. Macromolecules 2010, 43, 44-50
26. Zhang, C. Y.; Ling, J.; Wang, Q. Macromolecules 2011, 44, 8739-8743
27. Inoue, Y.; Watanabe, J.; Takai, M.; Yusa, S.; Ishihara, K. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 6073-6083
28. Song, A. R.; Parker, K. A.; Sampson, N. S. J. Am. Chem. Soc. 2009, 131, 3444-3445
29. Satoh, K.; Ozawa, S.; Mizutani, M.; Nagai, K.; Kamigaito, M. Nat. Commun. 2010, 1, 1-6
30. Satoh, K.; Matsuda, M.; Nagai, K.; Kamigaito, M. J. Am. Chem. Soc. 2010, 132, 10003-10005
31. Berthet, M. A.; Zarafshani, Z.; Pfeifer, S.; Lutz, J. F. Macromolecules 2010, 43, 44-50
32. Natalello, A.; Hall, J. N.; Eccles, E. A. L.; Kimani, S. M.; Hutchings, L. R. Macromol. Rapid Commun. 2011, 32, 233-237
33. Srichan, S.; Oswald, L.; Zamfir, M.; Lutz, J. F. Chem. Commun. 2012, 48, 1517-1519
34. Srichan, S.; Chan-Seng, D.; Lutz, J. F. ACS Macro Lett. 2012, 1, 589-592
35. Kleiner, R. E.; Brudno, Y.; Birnbaum, M. E.; Liu, D. R. J. Am. Chem. Soc. 2008, 130, 4646-4659
36. van Hest, J. C. M. Nat. Chem. Biol. 2008, 4, 272-273
37. Ida, S.; Terashima, T.; Ouchi, M.; Sawamoto, M. J. Am. Chem. Soc. 2009, 131, 10808-10809
38. Baughman, T. W.; Wagener, K. B. Adv. Polym. Sci. 2005, 176, 1-42
39. Zambelli, A.; Ammendola, P. Prog. Polym. Sci. 1991, 16, 203-218
40. Hatada, K. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 245-260
41. Coates, G. W. Chem. Rev. 2000, 100, 1223-1252
42. Kamigaito, M.; Satoh, K. Macromolecules 2008, 41, 269-276
43. Satoh, K.; Kamigaito, M. Chem. Rev. 2009, 109, 5120-5156
44. Schrock, R. R. Dalton Trans. 2011, 40, 7484-7495
45. Dijkstra, P. J.; Du, H. Z.; Feijen, J. Polym. Chem. 2011, 2, 520-527
46. Sita, L. R. Macromolecules 1995, 28, 656-657
47. Scherman, O. A.; Kim, H. M.; Grubbs, R. H. Macromolecules 2002, 35, 5366-5371
48. Scherman, O. A.; Walker, R.; Grubbs, R. H. Macromolecules 2005, 38, 9009-9014
49. Bielawski, C. W.; Grubbs, R. H. Prog. Polym. Sci. 2007, 32, 1-29
50. Kobayashi, S.; Pitet, L. M.; Hillmyer, M. A. J. Am. Chem. Soc. 2011, 133, 5794-5797
51. Martinez, H.; Miró, P.; Charbonneau, P.; Hillmyer, M. A.; Cramer, C. J. ACS Catal. 2012, 2, 2547-2556
52. Zhang, J.; Matta, M. E.; Hillmyer, M. A. ACS Macro Lett. 2012, 1, 1383-1387
53. We recently reported using this acetoxy system in the preparation of block copolymers. See: Pitet, L. M.; Zhang, J.; Hillmyer, M. A. Dalton Trans. 2013, 10.1039/C2DT32695G
54. Fink, J. K. Handbook of Engineering and Speciality Thermoplastics: Polyolejns and Styrenics; Scrivener Publishing LLC: Beverly, MA, 2010.
55. Rinno, H. Poly(Vinyl Esters). Ullmann's Encyclopedia of Industrial Chemistry: Wiley-VCH: Weinheim, Germany, 2000.
56. Cordeiro, C. F.; Petrocelli, F. P. Vinyl Acetate Polymers. Encyclopedia Of Polymer Science and Technology: Wiley-VCH: Weinheim, 2004.
57. Ito, S.; Munakata, K.; Nakamura, A.; Nozaki, K. J. Am. Chem. Soc. 2009, 131, 14606-14607
58. Mori, Y.; Sumi, H.; Hirabayashi, T.; Inai, Y.; Yokota, K. Macromolecules 1994, 27, 1051-1056
59. Hillmyer, M. A.; Laredo, W. R.; Grubbs, R. H. Macromolecules 1995, 28, 6311-6316
60. Lehman, S. E.; Wagener, K. B.; Baugh, L. S.; Rucker, S. P.; Schulz, D. N.; Varma-Nair, M.; Berluche, E. Macromolecules 2007, 40, 2643-2656
61. Watson, M. D.; Wagener, K. B. Macromolecules 2000, 33, 5411-5417
62. Hejl, A.; Scherman, O. A.; Grubbs, R. H. Macromolecules 2005, 38, 7214-7218
63. Hansson, S.; Heumann, A.; Rein, T.; Akermark, B. J. Org. Chem. 1990, 55, 975-984
64. Heumann, A.; Akermark, B.; Hansson, S.; Rein, T. Org. Synth. 1990, 68, 109-115
65. Morimoto, T.; Machida, T.; Hirano, M.; Zhung, X. M. J. Chem. Soc., Perkin Trans. 2 1988, 909-913
66. Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1992, 17, 1165-1167
67. Yokota, T.; Fujibayashi, S.; Nishiyama, Y.; Sakaguchi, S.; Ishii, Y. J. Mol. Catal. A: Chem. 1996, 114, 113-122
68. Macsari, I.; Szabo, K. J. Tetrahedron Lett. 1998, 39, 6345-6348
69. Cope, A. C.; Kinter, M. R.; Keller, R. T. J. Am. Chem. Soc. 1954, 76, 2757-2760
70. Cope, A. C.; Johnson, H. E. J. Am. Chem. Soc. 1957, 79, 3889-3892
71. Bielawski, C. W.; Hillmyer, M. A. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinham, Germany, 2003; Vol. 3, pp 255-282.
72. Hahn, S. F. J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 397-408
73. Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129-6139
74. Kawasaki, M.; Kakuda, H.; Goto, M.; Kawabata, S.; Kometani, T. Tetrahedron: Asym. 2003, 14, 1529-1534
75. Gais, H. J.; Jagusch, T.; Spalthoff, N.; Gerhards, F.; Frank, M.; Raabe, G. Chem.-Eur. J. 2003, 9, 4202-4221
76. Lussem, B. J.; Gais, H. J. J. Am. Chem. Soc. 2003, 125, 6066-6067
77. Lussem, B. J.; Gais, H. J. J. Org. Chem. 2004, 69, 4041-4052
78. Kasai, M.; Ziffer, H. J. Org. Chem. 1993, 48, 712-715
79. Asami, M. Bull. Chem. Soc. Jpn. 1990, 63, 721-727
80. Odian, G. Principles of Polymerization, 4 th ed.; Wiley-Interscience: New York, 2004.
81. Baughman, T. W.; Chan, C. D.; Winey, K. I.; Wagener, K. B. Macromolecules 2007, 40, 6564-6571
82. Opper, K. L.; Markova, D.; Klapper, M.; Mullen, K.; Wagener, K. B. Macromolecules 2010, 43, 3690-3698
83. Leonard, J. K.; Wei, Y. Y.; Wagener, K. B. Macromolecules 2012, 45, 671-680
84. Gospodinova, N.; Zlatkov, T.; Terlemezyan, L. Polymer 1998, 39, 2583-2588
85. Rojas, G.; Wagener, K. B. Macromolecules 2009, 42, 1934-1947
86. Yokota, K.; Kougo, T.; Hirabayashi, T. Polym. J. 1983, 15, 349-354
87. Wagener, K. B.; Valenti, D.; Hahn, S. F. Macromolecules 1997, 30, 6688-6690
88. Baughman, T. W.; Sworen, J. C.; Wagener, K. B. Macromolecules 2006, 39, 5028-5036
89. Peacock, A. Handbook of Polyethylene: Structures: Properties, and Applications, 1 st ed.; CRC Press: Boca Raton, FL, 2000.
90. Turner-Jones, A. J. Polym. Sci. 1962, 62, S53-S56
91. Seto, T.; Hara, T.; Tanaka, K. Jpn. J. Appl. Phys. 1968, 7, 31-42
92. Russell, K. E.; Hunter, B. K.; Heyding, R. D. Polymer 1997, 38, 1409-1414
93. Androsch, R.; Blackwell, J.; Chvalun, S. N.; Wunderlich, B. Macromolecules 1999, 32, 3735-3740
94. Lieser, G.; Wegner, G.; Smith, J. A.; Wagener, K. B. Colloid Polym. Sci. 2004, 282, 773-781
95. Rojas, G.; Inci, B.; Wei, Y. Y.; Wagener, K. B. J. Am. Chem. Soc. 2009, 131, 17376-17386
96. Buitrago, C. F.; Opper, K. L.; Wagener, K. B.; Winey, K. I. ACS Macro Lett. 2012, 1, 71-74
97. Inci, B.; Lieberwirth, I.; Steffen, W.; Mezger, M.; Graf, R.; Landfester, K.; Wagener, K. B. Macromolecules 2012, 45, 3367-3376
98. Kamath, P. M.; Wakefield, R. W. J. Appl. Polym. Sci. 1965, 9, 3153-3160
99. Peacock, A. J.; Mandelkern, L. J. Polym. Sci., Part B: Polym. Phys. 1990, 28, 1917-1941
100. Kennedy, M. A.; Peacock, A. J.; Mandelkern, L. Macromolecules 1994, 27, 5297-5310
101. Kennedy, M. A.; Peacock, A. J.; Failla, M. D.; Lucas, J. C.; Mandelkern, L. Macromolecules 1995, 28, 1407-1421