Degradable epoxy resins prepared from diepoxide monomer with dynamic covalent disulfide linkage

Polymer

Volumn 82, Issue , 2016, Pages 319-326

  Takahashi, Akira ^a   Ohishi, Tomoyuki ^a   Goseki, Raita ^a   Otsuka, Hideyuki ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Degradation; Dynamic covalent chemistry; Epoxy resins

Indexed keywords

COVALENT BONDS; DEGRADATION; EPOXY RESINS; TENSILE TESTING;

DIAMINE MOIETIES; DISULFIDE EXCHANGE; DISULFIDE LINKAGES; DYNAMIC COVALENT CHEMISTRY; LINEAR POLYMERS; NETWORK POLYMERS; STRUCTURAL CHARACTERIZATION; STRUCTURAL RIGIDITY;

SULFUR COMPOUNDS;

EID: 84949591163     PISSN: 00323861     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.polymer.2015.11.057     Document Type: Article

References (68)

1. X. Chen, M.A. Dam, K. Ono, A. Mal, H. Shen, F. Wudl, and et al. Science 295 2002 1698 1702
2. C.M. Chung, Y.S. Roh, S.Y. Cho, and J.G. Kim Chem. Mater. 16 2004 3982 3984
3. P. Cordier, F. Tournilhac, C. Soulié-Ziakovic, and L. Leibler Nature 451 2008 977 980
4. Y. Amamoto, J. Kamada, H. Otsuka, A. Takahara, and K. Matyjaszewski Angew. Chem. Int. Ed. 50 2011 1660 1663
5. M. Burnworth, L. Tang, J.R. Kumpfer, A.J. Duncan, S.J. Rowan, C. Weder, and et al. Nature 472 2011 334 337
6. K. Imato, M. Nishihara, T. Kanehara, Y. Amamoto, A. Takahara, and H. Otsuka Angew. Chem. Int. Ed. 51 2011 1138 1142
7. Y. Chen, A.M. Kushner, G.A. Williams, and Z. Guan Nat. Chem. 4 2012 467 472
8. Y. Amamoto, H. Otsuka, A. Takahara, and K. Matyjaszewski Adv. Mater. 24 2012 3975 3980
9. Y.-X. Lu, and Z. Guan J. Am. Chem. Soc. 134 2012 14226 14231
10. B.T. Michal, C.A. Jaye, E.J. Spencer, and S.J. Rowan ACS Macro Lett. 2 2013 694 699
11. M. Pepels, I. Filot, B. Klumperman, and H. Goossens Polym. Chem. 4 2013 4955 5011
12. C. Zeng, H. Seino, J. Ren, K. Hatanaka, and N. Yoshie Polymer 54 2013 5351 5357
13. A. Rekondo, R. Martin, A. Ruiz de Luzuriaga, G. Cabañero, H.J. Grande, and I. Odriozola Mater. Horiz. 1 2014 237 240
14. G. Deng, F. Li, H. Yu, F. Liu, C. Liu, W. Sun, and et al. ACS Macro Lett. 1 2012 275 279
15. Z.Q. Lei, H.P. Xiang, Y.J. Yuan, M.Z. Rong, and M.Q. Zhang Chem. Mater. 26 2014 2038 2046
16. K. Imato, A. Takahara, and H. Otsuka Macromolecules 48 2015 5632 5639
17. T.F. Scott, A.D. Schneider, W.D. Cook, and C.N. Bowman Science 308 2005 1615 1617
18. D. Montarnal, M. Capelot, F. Tournilhac, and L. Leibler Science 334 2011 965 968
19. M. Capelot, D. Montarnal, F. Tournilhac, and L. Leibler J. Am. Chem. Soc. 134 2012 7664 7667
20. Y.-X. Lu, F. Tournilhac, L. Leibler, and Z. Guan J. Am. Chem. Soc. 134 2012 8424 8427
21. J. Su, Y. Amamoto, T. Sato, T. Ohishi, A. Takahara, H. Otsuka, and et al. Polymer 55 2014 1474 1480
22. L. Imbernon, E.K. Oikonomou, S. Norvez, and L. Leibler Polym. Chem. 6 2015 4271 4278
23. D.A. Davis, A. Hamilton, J. Yang, L.D. Cremar, D. Van Gough, S.L. Potisek, and et al. Nature 459 2009 68 72
24. C.K. Lee, B.A. Beiermann, M.N. Silberstein, J. Wang, J.S. Moore, N.R. Sottos, and et al. Macromolecules 46 2013 3746 3752
25. K. Imato, A. Irie, T. Kosuge, T. Ohishi, A. Takahara, H. Otsuka, and et al. Angew. Chem. Int. Ed. 127 2015 6266 6270
26. X. Wang, F. Liu, X. Zheng, and J. Sun Angew. Chem. Int. Ed. 50 2011 11378 11381
27. H.G. Elias Macromolecules Application of Polymers vol. 4 2009 Wiley-VCH 303 370
28. S. Yang, J.-S. Chen, H. Körner, T. Breiner, C.K. Ober, and M.D. Poliks Chem. Mater. 10 1998 1475 1482
29. H. Okamura, S. Toda, M. Tsunooka, and M. Shirai J. Polym. Sci. Part A Polym. Chem. 40 2002 3055 3062
30. R. Giménez, X. Fernández-Francos, J.M. Salla, A. Serra, A. Mantecón, and X. Ramis Polymer 46 2005 10637 10647
31. L. Wang, and C.P. Wong J. Polym. Sci. Part A Polym. Chem. 37 1999 2991 3001
32. L. Wang, H. Li, and C.P. Wong J. Polym. Sci. Part A Polym. Chem. 38 2000 3771 3782
33. S.L. Buchwalter, and L.L. Kosbar J. Polym. Sci. Part A Polym. Chem. 34 1996 249 260
34. T. Hashimoto, H. Meiji, M. Urushisaki, T. Sakaguchi, K. Kawabe, C. Tsuchida, and et al. J. Polym. Sci. Part A Polym. Chem. 50 2012 3674 3681
35. A. Yamaguchi, T. Hashimoto, Y. Kakichi, M. Urushisaki, T. Sakaguchi, K. Kawabe, and et al. J. Polym. Sci. Part A Polym. Chem. 53 2015 1052 1059
36. Q. Tian, Y.C. Yuan, M.Z. Rong, and M.Q. Zhang J. Mater. Chem. 19 2009 1289 1298
37. Y. Min, S. Huang, Y. Wang, Z. Zhang, B. Du, X. Zhang, and et al. Macromolecules 48 2015 316 322
38. G.C. Tesoro, and V. Sastri J. Appl. Polym. Sci. 39 7 1990 1425 1437
39. V.R. Sastri, and G.C. Tesoro J. Appl. Polym. Sci. 39 7 1990 1439 1457
40. P.I. Engelberg, and G.C. Tesoro Polym. Eng. Sci. 30 5 1990 303 307
41. B.D. Fairbanks, S.P. Singh, C.N. Bowman, and K.S. Anseth Macromolecules 44 2011 2444 2450
42. S. Son, E. Shin, and B.-S. Kim Macromolecules 48 2015 600 609
43. R.E. Humphrey, and J.M. Hawkins Anal. Chem. 36 1964 1812 1814
44. R.E. Humphrey, and J.L. Potter Anal. Chem. 37 1965 164 165
45. W.J. Lees, and G.M. Whitesides J. Org. Chem. 58 1993 642 647
46. R. Singh, and L. Kats Anal. Biochem. 232 1995 86 91
47. S. Otto, R.L.E. Furlan, and J.K.M. Sanders J. Am. Chem. Soc. 122 2000 12063 12064
48. R.D. Bach, O. Dmitrenko, and C. Thorpe J. Org. Chem. 73 2008 12 21
49. R. Caraballo, M. Rahm, P. Vongvilai, T. Brinck, and O. Ramström Chem. Commun. 44 2008 6603 6605
50. M. Delius von, E.M. Geertsema, and D.A. Leigh Nat. Chem. 2 2009 96 101
51. H. Otsuka, S. Nagano, Y. Kobashi, T. Maeda, and A. Takahara Chem. Commun. 46 2010 1150 1152
52. A.M. Belenguer, T. Friščić, G.M. Day, and J.K.M. Sanders Chem. Sci. 2 2011 696 705
53. T. Mitamura, K. Iwata, and A. Ogawa J. Org. Chem. 76 2011 3880 3887
54. T. Ohishi, Y. Iki, K. Imato, Y. Higaki, A. Takahara, and H. Otsuka Chem. Lett. 42 2013 1346 1348
55. S.P. Black, J.K.M. Sanders, and A.R. Stefankiewicz Chem. Soc. Rev. 43 2014 1861 1872
56. A.M. Belenguer, G.I. Lampronti, D.J. Wales, and J.K.M. Sanders J. Am. Chem. Soc. 136 2014 16156 16166
57. F. Dénès, M. Pichowicz, G. Povie, and P. Renaud Chem. Rev. 114 2014 2587 2693
58. L.M. Johnson, E. Ledet, N.D. Huffman, S.L. Swarner, S.D. Shepherd, P.G. Durham, and et al. Polymer 64 2015 84 92
59. C. Grave, I. McEwan, and R.A. Pethrick J. Appl. Polym. Sci. 69 1998 2369 2376
60. M.R. Vanlandingham, R.F. Eduljee, and J.W. Gillespie J. Appl. Polym. Sci. 71 1999 787 798
61. Y. Zhou, C. Jiang, Y. Zhang, Z. Liang, W. Liu, L. Wang, and et al. J. Med. Chem. 53 2010 5449 5466
62. T. Miyashita, M. Matsuda, and M. Iino Bull. Chem. Soc. Jpn. 48 1975 3230 3235
63. A. Schönberg, and A. Mustafa J. Am. Chem. Soc. 73 1951 2401-2401
64. S. Vyazovkin, and N. Sbirrazzuoli Macromolecules 29 1996 1867 1873
65. X. Wang, K. Yang, J. Kumar, S.K. Tripathy, K.G. Chittibabu, L. Li, and et al. Macromolecules 31 1998 4126 4134
66. F.E. Oleinik Epoxy-aromatic Amine Networks in the Glassy State Structure and Properties: Epoxy Resins and Composites IV 1986 Springer Berlin Heidelberg 49 99
67. C. Fromonteil, and P. Bardelle Cansell Ind. Eng. Chem. Res. 39 2000 922 925
68. G. Jiang, S.J. Pickering, E.H. Lester, and N.A. Warrior Ind. Eng. Chem. Res. 49 2010 4535 4541