Reversibly cross-linking amino-polysiloxanes by simple triatomic molecules. facile methods for tuning thermal, rheological, and adhesive properties

Journal of Physical Chemistry C

Volumn 113, Issue 27, 2009, Pages 11546-11553

  Yu, Tao ^a   Wakuda, Koji ^a   Blair, Daniel L ^b   Weiss, Richard G ^a  

^a GEORGETOWN UNIVERSITY   (United States)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADHESIVE PROPERTIES; AMINO FUNCTIONAL GROUP; AMINO GROUP; AMMONIUM CARBAMATES; CHEMICAL CHANGE; DITHIOCARBAMATES; FACILE METHOD; FLOWING LIQUID; IONIC CROSS-LINKS; LENGTH SCALE; NANOMETRIC; NEW MATERIAL; PARENT POLYMERS; POLYMER CHAINS; POLYMER SIDE-CHAINS; POLYSILOXANES; PROTONATED; ROOM TEMPERATURE; RUBBERLIKE MATERIALS; SILOXANE POLYMERS; TRIATOMIC MOLECULES; USEFUL PROPERTIES;

AMINATION; AMINES; AMMONIUM COMPOUNDS; CARBON MONOXIDE; FUNCTIONAL GROUPS; FUNCTIONAL POLYMERS; GELATION; HEATING; IONIZATION OF LIQUIDS; LIQUIDS; PHOTORESISTS; PHYSICAL PROPERTIES; POLYMERS; RHEOLOGY; SILANES; SILICONES; SWELLING; THIOUREAS; UREA;

MATERIALS PROPERTIES;

EID: 67650787031     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp900115g     Document Type: Article

References (86)

1. (a) Silicon-Based Polymer Science: A comprehensive resource; Advances in Chemistry Series 224; Zeigler, J. M., Fearon, F. W. G., Eds.; American Chemical Society: Washington, DC, 1990.
2. (b) Clarson, S. J.; Smith, S. D.; Owen, M. J. Silicones and Silicone-Modified Materials; American Chemical Society: Washington, DC, 2000.
3. (c) Manners, I. Angew. Chem., Int. Ed. 1996, 35, 1602-1621.
4. (d) Mark, J. E. Acc. Chem. Res. 2004, 37, 946-953.
5. Physical Properties of Polymers Handbook, 2nd ed.; Mark, J. E., Ed.; Springer: Berlin, Germany, 2007.
6. (b) Mark, J. E.; Allcock, H. R.; West, R. Inorganic Polymers, 2nd ed.; Oxford University Press: New York, 2005; pp 154-199.
7. (c) Erman, B.; Mark, J. E. Structures and Properties of Rubberlike Networks; Oxford University Press: New York, 1997.
8. Gao, Z.; Nahrup, J. S.; Mark, J. E.; Sakr, A. J. Appl. Polym. Sci. 2003, 90, 658-666.
9. Batra, A.; Cohen, C.; Archer, L. A. Macromolecules 2005, 38, 7174-7180.
10. (a) Kato, D.; Masaike, M.; Majima, T.; Hirata, Y.; Mizutani, F.; Sakata, M.; Hirayama, C.; Kunitake, M. Chem. Commum. 2002, 2616, 2617.
11. (b) Park, H. B.; Kim, J. K.; Nam, S. Y.; Lee, Y. M. J. Membr. Sci. 2003, 220, 59-73.
12. (c) Miller, A. L., II; Bowden, N. B. Chem. Commum. 2007, 20, 2051-2053.
13. Verma, M. K. S.; Majumder, A.; Ghatak, A. Langmuir 2006, 22, 10291-10295.
14. Oomen, A. G.; Mayer, P.; Tolls, J. Anal. Chem. 2000, 72, 2802-2808.
15. (a) Paul, K. E.; Prentiss, M.; Whitesides, G. M. Adv. Funct. Mater. 2003, 13, 259-263.
16. (b) Mcdonald, J. C.; Whitesides, G. M. Acc. Chem. Res. 2002, 35, 491-499.
17. (a) Cho, S. H.; Andersson, H. M.; White, S. R.; Sottos, N. R.; Braun, P. V. Adv. Mater. 2006, 18, 997-1000.
18. (b) Wu, D. Y.; Meure, S.; Solomon, D. Prog. Polym. Sci. 2008, 33, 479-522.
19. (a) Abe, Y.; Gunji, T. Prog. Polym. Sci. 2004, 29, 149-182.
20. (b) Abbasi, F.; Mirzadeh, H.; Katbab, A. A. Polym. Int. 2001, 50, 1279-1287.
21. (a) Zhang, X.; Xie, P.; Shen, Z.; Jiang, J.; Zhu, C.; Li, H.; Zhang, T.; Han, C. C.; Wan, L.; Yan, S.; Zhang, R. B. Angew. Chem., Int. Ed. 2006, 45, 3112-3116.
22. (b) Zhou, Q. L.; Yan, S. K.; Han, C. C.; Xie, P.; Zhang, R. B. Adv. Mater. 2008, 20, 2970-2976.
23. (a) Zhang, Z. C.; Sherlock, D.; West, R.; West, R.; Amine, K.; Lyons, L. J. Macromolecules 2003, 36, 9176-9180.
24. (b) Ngoumeni-Yappi, R.; Fasel, C.; Riedel, R.; Ischenko, V.; Pippel, E.; Woltersdorf, J.; Clade, J. Chem. Mater. 2008, 20, 3601-3608.
25. Zhang, Y.; Cao, M.; Guo, G. Q.; Sun, J.; Li, Z.; Xie, P.; Zhang, R. B.; Fu, P. F. J. Mater. Chem. 2002, 12, 2325-2330.
26. Nair, K. P.; Breedveld, V.; Weck, M. Macromolecules 2008, 41, 3429-3438.
27. Serpe, M. J.; Craig, S. L. Langmuir 2007, 23, 1626-1634.
28. (a) George, M.; Weiss, R. G. J. Am. Chem. Soc. 2001, 123, 10393-10394.
29. (b) George, M.; Weiss, R. G. Langmuir 2002, 18, 7124-7135.
30. (c) Carretti, E.; Dei, L.; Baglioni, P.; Weiss, R. G. J. Am. Chem. Soc. 2003, 125, 5121-5129.
31. (a) Yamada, T.; Lukac, P. J.; George, M.; Weiss, R. G. Chem. Mater. 2007, 19, 967-969.
32. (b) Yamada, T.; Lukac, P. J.; Yu, T.; Weiss, R. G. Chem. Mater. 2007, 19, 4761-4768.
33. (c) Yu, T.; Yamada, T.; Gaviola, C. G.; Weiss, R. G. Chem. Mater. 2008, 20, 5337-5344.
34. (a) Jessop, P. G.; Heldebrant, D. J.; Li, X.; Eckert, C. A.; Liotta, C. L. Nature (London) 2005, 436, 1102.
35. (e) Phan, L.; Andreatta, J. R.; Horvey, L. K.; Edie, C. F.; Luco, A.-L.; Mirchandani, A.; Darensbourg, D. J.; Jessop, P. G. J. Org. Chem. 2008, 73, 127-132.
36. (a) Endo, T.; Nagai, D.; Monma, T.; Yamaguchi, H.; Ochiai, B. Macromolecules 2004, 37, 2007-2009.
37. (b) Ochiai, B.; Yokota, K.; Fujii, A.; Nagai, D.; Endo, T. Macromolecules 2008, 41, 1229-1236.
38. (a) Xu, H.; Hampe, E. M.; Rudkevich, D. M. Chem. Commum. 2003, 2828-2829.
39. (b) Xu, H.; Rudkevich, D. M. Chems-Eur. J. 2004, 10, 5432-5442.
40. (c) Rudkevich, D. M.; Xu, H. Chem. Commum. 2005, 2651-2659.
41. (a) Hori, Y.; Nagano, Y.; Nakao, J.; Taniguchi, H. Chem. Express 1986, 1, 173-176.
42. (b) Hori, Y.; Nagano, Y.; Nakao, J.; Fukuhara, T.; Taniguchi, T. Chem. Express. 1986, 1, 224-227.
43. (c) Dell'Amico, D. B.; Calderazzo, F.; Labella, L.; Marchetti, F.; Pampaloni, G. Chem. Rev. 2003, 103, 3857-3897.
44. George, M.; Weiss, R. G. Langmuir 2003, 19, 1017-1025.
45. Laidler, K. J.; Meiser, J. H. Physical Chemistry, 3rd ed.; Houghton Mufflin: Boston, MA, 1999; p 267
46. DeLassus, P. T.; Whiteman, N. F. In Polymer Handbook; Brandrup, J., Immergut, E. H., Grulke, E. A., Eds.; Wiley: New York, 1999; p V/168.
47. Schroeder, D. C. Chem. Rev. 1955, 55, 181-228.
48. House, H. O. Modern Synthetic Reaction, 2nd ed.; W. A. Benjamin: Menlo Park, CA, 1972; p 2.
49. Corset, C.; Froment, F. J. Phys. Chem. 1990, 94, 6908-6911.
50. Lobo, H.; Bonilla, J. V. Handbook of Plastics Analysis; Marcel Dekker: New York, 2003.
51. (a) Nakamoto, K.; Fujita, J.; Condrate, R. A.; Morimoto, Y. J. Chem. Phys. 1963, 39, 423-427.
52. (b) Gosavi, R. K.; Agarwala, U.; Rao, C. N. R. J. Am. Chem. Soc. 1967, 89, 235-239.
53. Boas, U.; Karlsson, A. J.; de Waal, B. F. M.; Meijer, E. W. J. Org. Chem. 2001, 66, 2136-2145.
54. George, M.; Weiss, R. G. Langmuir 2003, 19, 1017-1025.
55. Guadagno, T.; Kazarian, S. G. J. Phys. Chem. B 2004, 108, 13995-13999.
56. (a) Brennan, D. P.; Dobley, A.; Sideris, P. J.; Oliver, S. R. Langmuir 2005, 21, 11994-11998.
57. (b) Favre, E. Eur. Polym. J. 1996, 32, 1183-1188.
58. (a) Sonmez, H. M.; Wudl, F. Macromolecules 2005, 38, 1623-1626.
59. (b) Wang, C.; Li, Y.; Hu, Z. Macromolecules 1997, 30, 4727-4732.
60. 35a,b second law because the samples employed do not have constant thicknesses.
61. (a) Comyn, J. Polymer permeability; Elsevier: London, U.K., 1985.
62. (b) Crank, J. The Mathematics of Diffusion; Oxford University Press: Oxford, U.K., 1975.
63. Khan, S. A.; Royer, J. R.; Raghavan, S. R. Aviation Fuels with Improved Fire Safety: A Proceeding; National Academy Press: Washington, DC, 1997; pp 3146.
64. Carraher, C. E. Seymour/Carraher's polymer chemistry, 7th ed.; CRC Press: Boca Raton, FL, 2008; pp 4982.
65. Custelcean, R. Chem. Commum. 2008, 295, 307.
66. (a) Menger, F. M.; Caran, K. L. J. Am. Chem. Soc. 2000, 122, 11679-11691.
67. (b) Yabuuchi, K.; Marfo-Owusu, E.; Kato, T. Org. Biomol. Chem. 2003, 1, 3464-3469.
68. (c) Pèrez-Folch, J.; Subirana, J. A.; Aymami, J. J. Chem. Crystallogr. 1997, 27, 367-369.
69. (d) Ramanathan, A.; Siakumar, K.; Subramanian, K.; Janarthanan, N.; Ramadas, K.; Fun, H.-K. Acta Cryatallogr. Sect. C 1995, 51, 2446-2450.
70. (a) Ketner, A. M.; Kumar, R.; Davies, T. S.; Elder, P. W.; Raghavan, S. R. J. Am. Chem. Soc. 2007, 129, 1553-1559.
71. (b) Tung, S. H.; Huang, Y. E.; Raghavan, S. R. Langmuir 2007, 23, 372-376.
72. (c) Tung, S. H.; Huang. Y. E.; Raghavan, S. R. Soft Matter 2008, 4, 1086-1093.
73. (a) Macosko, C. W. Rheology: Principles, Measurements and Applications; VCH Publishers: New York, 1994.
74. (b) Winter, H. H.; Chambon, F. J. Rheol. 1986, 30, 367-382.
75. (a) Hyun, K.; Kim, S. H.; Ahn, K. H.; Lee, S. J. J. Non-Newtonian Fluid Mech. 2002, 107, 51-65.
76. (b) Sim, H. G.; Ahn, K. H.; Lee, S. J. J Non-Newtonian Fluid Mech. 2003, 112, 237-250.
77. Veselovskii, R. A. Adhesion of polymers; McGraw-Hill: New York, 2002.
78. Carretti, E; Dei, L; Macherelli, A.; Weiss, R. G. Langmuir 2004, 20, 8414-8418.
79. Khongtong, S.; Ferguson, G. S. J. Am. Chem. Soc. 2002, 124, 7254-7255.
80. 2, and their adhesive strength can be tuned by changing the temperature.
81. (a) Carretti, E.; Dei, L.; Weiss, R. G. Soft Matter 2005, 1, 17-22.
82. (b) Carretti, E.; Dei, L.; Weiss, R. G.; Baglioni, P. J. Cult. Heritage 2008, 9, 386-393.
83. Chang-Chien, G. P.; Lee, W. S.; Tsai, J. L.; Jeng, S. H. J. Chromatogr. A 2001, 932, 97-105.
84. Freudenberger, J. V.; Spiteller, P.; Bauer, R.; Kessler, H.; Luy, B. J. Am. Chem. Soc. 2004, 126, 14690-14691.
85. (a) Alauzun, J.; Besson, E.; Mehdi, A.; Reyè, C.; Corriu, R. J. P. Chem. Mater. 2008, 20, 503-513.
86. (b) Soutullo, M. D.; Odom, C. I.; Wicker, B. F.; Henderson, C. N.; Stenson, A. C.; Davis, J. H. Chem. Mater. 2007, 19, 3581-3583.