Thermally amendable tailor-made functional polymer by RAFT polymerization and "click reaction"

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 51, Issue 16, 2013, Pages 3365-3374

  Pramanik, Nabendu B ^a   Bag, Dibyendu S ^b   Alam, Sarfaraz ^b   Nando, Golok B ^a   Singha, Nikhil K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

^b DEFENCE MATERIALS AND STORES RESEARCH AND DEVELOPMENT ESTABLISHMENT   (India)

Author keywords

crosslinking; Diels Alder polymers; reversible addition fragmentation chain transfer (RAFT)

Indexed keywords

DIELS-ALDER POLYMERS; DIELS-ALDER REACTION; MATRIX-ASSISTED LASER DESORPTION IONIZATION; RAFT POLYMERIZATION; TAILOR-MADE POLYMERS; THERMAL INITIATORS; THERMOREVERSIBLE; TIME OF FLIGHT MASS SPECTROMETRY;

FREE RADICAL POLYMERIZATION; FUNCTIONAL POLYMERS; LIVING POLYMERIZATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYACRYLATES;

CROSSLINKING;

EID: 84879845031     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.26732     Document Type: Article

References (98)

1. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
2. (a), M. A. Gauthier, M. I. Gibson, H. A. Klok, Angew. Chem. Int. Ed. 2009, 48, 48-58
3. (b), H. Nandivada, X. Jiang, J. Lahann, Adv. Mater. 2007, 19, 2197-2208
4. (c), H. Durmaz, F. Karatas, U. Tunca, G. Hizal, J. Polym. Sci. Part A: Polym. Chem. 2006, 44, 499-509
5. (d), T. D. Kim, J. Luo, Y. Tian, J. W. Ka, N. M. Tucker, M. Haller, J.-W. Kang, A. K. Y. Jen, Macromolecules 2006, 39, 1676-1680
6. (e), J. R. Mcelhanon, D. R. Wheeler, Org. Lett. 2001, 3, 2681-2683.
7. (a), J. F. Lutz, Angew. Chem. Int. Ed. 2007, 46, 1018-1025
8. (b), V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2596-2599
9. (c), C. W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064.
10. (a), L. M. Campos, K. L. Killops, R. Sakai, J. M. J. Paulusse, D. Damiron, E. Drockenmuller, B. W. Messmore, C. J. Hawker, Macromolecules 2008, 41, 7063-7070
11. (b), K. L. Killops, L. M. Campos, C. J. Hawker, J. Am. Chem. Soc. 2008, 130, 5062-5064
12. (c), S. P. S. Koo, M. M. Stamenovic, R. A. Prasath, A. J. Inglis, F. E. Du Prez, C. Barner-Kowollik, W. Van Camp, T. Junkers, J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 1699-1713.
13. (a), B. M. Rosen, G. Lligadas, C. Hahn, V. Percec, J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 3940-3948
14. (b), B. M. Rosen, G. Lligadas, C. Hahn, V. Percec, J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 3931-3939.
15. C. M. Dry, N.R. Sottos, Technomic 1992, 438-444.
16. C. M. Dry, J. Intell. Matter. Syst. Struct. 1993, 420-425.
17. Self Healing Materials;, S. V. D. Zwaag, Eds.; Springer Series in Materials Science: Springer: Noordwijk, Netherlands, 2007; Vol. 100.
18. Y. L. Liu, Y. W. Chen, Macromol. Chem. Phys. 2007, 208, 224-232.
19. A. A. Kavitha, N. K. Singha, Macromolecules 2010, 43, 3193-3205.
20. A. A. Kavitha, N. K. Singha, ACS Appl. Mater. Interfaces 2009, 1, 1427-1436.
21. K. Jud, H. H. Kausch, J. G. Williams, J. Mater. Sci. 1981, 16, 204-210.
22. C. Dry, Comp. Struct. 1996, 35, 263-264.
23. J. Raghavan, R. P. Wool, J. Appl. Polym. Sci. 1999, 71, 775-785.
24. (a), P. Cordier, F. Tournilhac, C. Soulie'-Ziakovic, L. Leibler, Nature 2008, 451, 977-980
25. (b), D. Montarnal, P. Cordier, C. Soulie'-Ziakovic, F. Tournilhac, L. Leibler, J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 7925-7936
26. (c), F. Tournilhac, P. Cordier, D. Montarnal, C. Soulié-Ziakovic, L. Leibler, Macromol. Symp. 2010, 291-292, 84-88.
27. J. A. Syrett, C. R. Becer, D. M. Haddleton, Polym. Chem. 2010, 1, 978-987.
28. J. A. Syrett, G. Mantovani, W. R. S. Barton, D. Price, D. M. Haddleton, Polym. Chem. 2010, 1, 102-106.
29. K. M. Wiggins, J. A. Syrett, D. M. Haddleton, C. W. Bielawski, J. Am. Chem. Soc. 2011, 133, 7180-7189.
30. (a), S. R. White, N. R. Sottos, P. H. Geubelle, J. S. Moore, M. R. Kessler, S. R. Sriram, E. N. Brown, S. Viswanathan, Nature 2001, 409, 794-797
31. (b), K. S. Toohey, N. R. Sottos, J. A. Lewis, J. S. Moore, S. R. White, Nat. Mater. 2007, 6, 581-585
32. (c), I. Yang, M. W. Keller, J. S. Moore, S. R. White, N. R. Sottos, Macromolecules 2008, 41, 9650-9655
33. (d), S. A. Odom, S. Chayanupatkul, B. J. Blaiszik, O. Zhao, A. C. Jackson, P. V. Braun, N. R. Sottos, S. R. White, J. S. Moore, Adv. Mater. 2012, 24, 2578-2581
34. (e), H. Jin, C. L. Mangun, D. S. Stradley, J. S. Moore, N. R. Sottos, S. R. White, Polymer 2012, 53, 581-587.
35. Y. Chujo, K. Sada, T. Saegusa, Macromolecules 1990, 23, 2636-2641.
36. H. Laita, S. Boufi, A. Gandini, Eur. Polym. J. 1997, 33, 1203-1211.
37. C. Gousse, A. Gandini, Polym. Int. 1999, 48, 723-731.
38. Y. Imai, H. Itoh, K. Naka, Y. Chujo, Macromolecules 2000, 33, 4343-4346.
39. (a), X. Chen, M. A. Dam, K. Ono, A. Mal, H. Shen, S. R. Nutt, K. Sheran, F. Wudl, Science 2002, 295, 1698-1702
40. (b), X. Chen, F. Wudl, A. K. Mal, H. Shen, S. R. Nutt, Macromolecules 2003, 36, 1802-1807
41. (c), S. D. Bergman, F. Wudl, J. Mater. Chem. 2008, 18, 41-62
42. (d), B. Veldman, T. Kaully, R. K. Feller, E. Falcao, F. Wudl, Macromolecules 2009, 42, 6848-6850
43. (e), E. B. Murphy, F. Wudl, Prog. Polym. Sci. 2010, 35, 223-251.
44. H. Durmaz, A. Sanyal, G. Hizal, U. Tunca, Polym. Chem. 2012, 3, 825-835.
45. A. Sanyal, Macromol. Chem. Phys. 2010, 211, 1417-1425.
46. T. Dispinkar, R. Sanyal, A. Sanyal, J. Polym. Sci. Part A: Polym. Chem. 2007, 45, 4545-4551.
47. X. Chen, F. Wudl, A. K. Mal, H. Shen, S.R. Nutt, Macromolecules 2003, 36, 1802-1807.
48. E. Goiti, M. B. Huglin, J. M. Rego, Macromol. Rapid Commun. 2003, 24, 692-696.
49. K. Adachi, A. K. Achimuthu, Y. Chujo, Macromolecules 2004, 37, 9793-9797.
50. E. Goiti, M. B. Huglin, J. M. Rego, Eur. Polym. J. 2004, 40, 219-226.
51. S. Abid, R. E. Gharbi, A. Gandini, Polymer 2004, 45, 6469-6478.
52. E. Goiti, F. Heatley, M. B. Huglin, J. M. Rego, Eur. Polym. J. 2004, 40, 1451-1460.
53. N. Davidenko, D. Zaldivar, C. Peniche, R. Sastre, J. S. Roman, J. Polym. Sci. Part A: Polym. Chem. 1996, 34, 2759-2766.
54. E. Goiti, M. B. Huglin, J. M. Rego, Polymer 2001, 42, 10187-10193.
55. M. Dellerba, J. R. Ebdon, S. Rimmer, Macromol. Rapid Commun. 1997, 18, 723-728.
56. (a), K. Matyjaszewski, Controlled Radical Polymerization; ACS Symposium Series: American Chemical Society: Washington, DC, 1997; Vol. 685
57. (b), K. A. Davis, K. Matyjaszewski, Statistical, Gradient, Block and Graft Copolymers by Controlled/Living Radical Polymerizations; Spinger-Verlag: Berlin, Heidelberg, 2002; Vol. 159.
58. (a), C. J. Hawker, A. W. Bosman, E. Harth, Chem. Rev. 2001, 101, 3661-3688
59. (b), C. J. Hawker, Acc. Chem. Res. 1997, 30, 373-382.
60. (a), K. Matyjaszewski, J. Xia, Chem. Rev. 2001, 101, 2921-2990
61. (b), M. Kamigaito, T. Ando, M. Sawamoto, Chem. Rev. 2001, 101, 3689-3745
62. (c), V. Cossens, T. Pintauer, K. Matyjaszewski, Prog. Polym. Sci. 2001, 26, 337-377.
63. (a), V. Percec, B. Barboiu, Macromolecules 1995, 28, 7970-7972
64. (b), V. Percec, B. Barboiu, H.-J. Kim, J. Am. Chem. Soc. 1998, 120, 305-316
65. (c), V. Percec, H.-J. Kim, B. Barboiu, Macromolecules 1997, 30, 8526-8528
66. (d), V. Percec, A. D. Asandei, F. Asgarzadeh, T. K. Bera, B. Barboiu, J. Polym. Sci. Part A: Polym. Chem. 2000, 38, 3839-3843.
67. (a), G. Moad, E. Rizzardo, S. H. Thang, Aust. J. Chem. 2005, 58, 379-410
68. (b), G. Moad, E. Rizzardo, S. H. Thang, Aust. J. Chem. 2006, 59, 669-692
69. (c) Handbook of RAFT Polymerization;, C. Barner-Kowollik, Eds.; Wiley-VCH: Weinheim, 2008.
70. (a), V. Percec, A. V. Popov, E. Ramirez-Castillo, M. Monteiro, B. Barboiu, O. Weichold, A. D. Asandei, C. M. Mitchell, J. Am. Chem. Soc. 2002, 124, 4940-4941
71. (b), V. Percec, T. Guliashvili, J. S. Ladislaw, A. Wistrand, A. Stjerndahl, M. J. Sienkowska, M. J. Monteiro, S. Sahoo, J. Am. Chem. Soc. 2006, 128, 14156-14165
72. (c), B. M. Rosen, V. Percec, Chem. Rev. 2009, 109, 5069-5119
73. (d), N. H. Nguyen, M. E. Levere, J. Kulis, M. J. Monteiro, V. Percec, Macromolecules 2012, 45, 4606-4622
74. (e), M. E. Levere, N. H. Nguyen, X. Leng, V. Percec, Polym. Chem. 2013, 4, 1635-1647.
75. A. A. Kavitha, N. K. Singha, J. Polym. Sci. Part A: Polym. Chem. 2007, 45, 4441-4449.
76. C. L. McCormick, B. S. Sumerlin, B. S. Lokitz, J. E. Stempka, Soft. Matter 2008, 4, 1760-1773.
77. A. W. York, S. E. Kirklan, C. L. McCormick, Adv. Drug Delivery Rev. 2008, 60, 1018-1036.
78. G. Moad, G. Li, R. Pfaendner, A. Postma, E. Rizzardo, S. Thang, H. Wermter, ACS Symp. Ser. 2006, 944, 514-532.
79. L. Barner, T. P. Davis, M. H. Stenzel, C. Barner-Kowollik, Macromol. Rapid Commun. 2007, 28, 539-559.
80. M. H. Stenzel, Chem. Commun. 2008, 3486-3503.
81. A. W. York, S. E. Kirkland, C. L. McCormick, Adv. Drug Delivery Rev. 2008, 60, 1018-1036.
82. J. Chiefari, Y. K. Chong, F. Ercole, J. Krstina, J. Jeffery, T. P. T. Le, R. T. A. Mayadunne, G. F. Meijs, C. L. Moad, G. Moad, E. Rizzardo, S. H. Thang, Macromolecules 1998, 31, 5559-5562.
83. M. I. Gibson, E. Fröhlich, H. A. Klok, J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 4332-4345.
84. P. J. Flory, J. Rehner, J. Chem. Phys. 1943, 11, 521-526.
85. S. D. Tobing, A. Klein, J. Appl. Polym. Sci. 2000, 76, 1965-1976.
86. G. V. Schulz, H. Z. Doll, Elektrochem. 1952, 56, 248-257.
87. B. S. Rao, R. Sireesha, A. R. Pasala, Polym. Int. 2005, 54, 1103-1109.
88. Y. Mitsukami, M. S. Donovan, A. B. Lowe, C. L. McCormick, Macromolecules 2001, 48, 2248-2256.
89. Y. Luo, B. Liu, Z. Wang, J. Gao, B. Li, J. Polym. Sci. Part A: Polym. Chem. 2007, 45, 2304-2315.
90. K. Soga, H. Deng, T. Yano, T. Shiono, Macromolecules 1994, 27, 7938-7940.
91. R. Potzsch, S. Fleischmann, C. Tock, H. Komber, B. Voit, Macromolecules 2011, 44, 3260-3269.
92. G. Zhou, I. I. Harruna, Anal. Chem. 2007, 79, 2722-2727.
93. X. Jiang, P. J. Schonenmakers, J. L. J. van Dongen, X. Lou, V. Lima, J. Brokken-Zijp, Anal. Chem. 2003, 75, 5517-5524.
94. E. Beyou, P. Chaumont, F. Chauvin, C. Devaux, N. Zydowicz, Macromolecules 1998, 31, 6828-6835.
95. R. Gheneim, C. P. Berumen, A. Gandini, Macromolecules 2002, 35, 7246-7253.
96. C. Tarducci, J. P. S. Badyal, S. A. Brewerb, C. Willis, Chem. Commun. 2005, 406, 406-408.
97. D. Lin-Vien, N. B. Colthup, W. G. Fateley, J. G. Grassetti, The Handbook of Infrared; Raman Characteristic Frequencies of Organic Molecules; Academic Press: New York, 1991.
98. Y. Liu, D. Hsieh, J. Polym. Sci. Part A: Polym. Chem. 2006, 44, 905-913.