Polycyanurate networks with enhanced segmental flexibility and outstanding thermochemical stability

Macromolecules

Volumn 45, Issue 24, 2012, Pages 9707-9718

  Guenthner, Andrew J ^a   Davis, Matthew C ^b   Ford, Michael D ^b   Reams, Josiah T ^a   Groshens, Thomas J ^b   Baldwin, Lawrence C ^b   Lubin, Lisa M ^c   Mabry, Joseph M ^a  

^a AIR FORCE RESEARCH LABORATORY   (United States)

^b NAVAL AIR WARFARE CENTER   (United States)

^c AIR FORCE RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC CONTENTS; CROSS-LINK DENSITIES; CYANATE ESTERS; EXTENT OF CURE; FLEXIBLE NETWORKS; HIGH TEMPERATURE; MOISTURE UPTAKE; OPTIMAL COMBINATION; POLYCYANURATES; PROCESS CONDITION; THERMO-CHEMICAL STABILITY; THERMO-MECHANICAL; THERMOSETTING POLYMERS;

BENZENE; CARBON CARBON COMPOSITES; CURING; ESTERS; ETHANE; THERMOSETS;

GLASS TRANSITION;

EID: 84871570118     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma302300g     Document Type: Article

References (57)

1. Hamerton, I. Chemistry and Technology of Cyanate Ester Resins; Chapman & Hall: London, 1994.
2. Nair, C. P. R.; Mathew, D.; Ninan, K. N. Cyanate ester resins, recent developments. In New Polymerization Techniques and Synthetic Methodologies; Springer: Berlin, 2001; Vol. 155, pp 1-99.
3. Fang, T.; Shimp, D. A. Prog. Polym. Sci. 1995, 20, 61-118
4. Yameen, B.; Duran, H.; Best, A.; Jonas, U.; Steinhart, M.; Knoll, W. Macromol. Chem. Phys. 2008, 209, 1673-1685
5. Ganguli, S.; Dean, D.; Jordan, K.; Price, G.; Vaia, R. Polymer 2003, 44 (22) 6901-6911
6. Shivakumar, K. N.; Chen, H.; Holloway, G. J. Reinf. Plast. Compos. 2009, 28, 675-689
7. Chen, H.; Shivakumar, K. Proc. 22nd Am. Soc. Compos., Tech. Conf. 2007, 93/1-93/18
8. Chen, H. C. CMC-Comput. Mater. Contin 2008, 8, 33-42
9. Gitsas, A.; Yameen, B.; Lazzara, T. D.; Steinhart, M.; Duran, H.; Knoll, W. Nano Lett. 2010, 10, 2173-2177
10. Fyfe, C. A.; Niu, J.; Rettig, S. J.; Burlinson, N. E.; Reidsema, C. M.; Wang, D. W.; Poliks, M. Macromolecules 1992, 25, 6289-6301
11. Snow, A. W.; Armistead, J. P. Naval Research Laboratory Memorandum Report 6848; Naval Research Laboratory: Washington, DC, 1991.
12. Shimp, D. A.; Craig, W. M. New Liquid Dicyanate Monomer for Rapid Impregnation of Reinforcing Fibers. In 34th International SAMPE Symposium; SAMPE International: Long Beach, CA, 1989; pp 1336-1346.
13. Reams, J. T.; Guenthner, A. J.; Lamison, K. R.; Vij, V.; Lubin, L. M.; Mabry, J. M. ACS Appl. Mater. Interfaces 2012, 4, 527-535
14. Marella, V. V. An Investigation on the Hydrolysis of Polyphenolic Cyanate Esters using Near-IR Spectroscopy. M.S. Thesis, Drexel University, Philadelphia, PA, 2008.
15. Guenthner, A. J.; Lamison, K. R.; Davis, M. C.; Cambrea, L. R.; Yandek, G. R.; Mabry, J. M. In Cure Characteristics of Tricyanate Ester High-Temperature Composite Resins; 2011, SAMPE Spring Technical Conference and Exhibition-State of the Industry: Advanced Materials, Applications, and Processing Technology, Long Beach, CA; SAMPE International Business Office: Long Beach, CA, 2011; paper 56-1681.
16. Mondragon, I.; Solar, L.; Recalde, I. B.; Gómez, C. M. Thermochim. Acta 2004, 417, 19-26
17. Teil, H.; Page, S. A.; Michaud, V.; MaÌŠnson, J. A. E. J. Appl. Polym. Sci. 2004, 93, 1774-1787
18. Zhao, L.; Hu, X. A. Polymer 2010, 51, 3814-3820
19. Corezzi, S.; Fioretto, D.; Santucci, G.; Kenny, J. M. Polymer 2010, 51, 5833-5845
20. Kasehagen, L. J.; Haury, I.; Macosko, C. W.; Shimp, D. A. J. Appl. Polym. Sci. 1997, 64, 107-113
21. Georjon, O.; Galy, J. Polymer 1998, 39, 339-345
22. Guenthner, A. J.; Davis, M. C.; Lamison, K. R.; Yandek, G. R.; Cambrea, L. R.; Groshens, T. J.; Baldwin, L. C.; Mabry, J. M. Polymer 2011, 52, 3933-3942
23. Al-Saleh, B.; Abdelkhalik, M. M.; Eltoukhy, A. M.; Elnagdi, M. H. J. Heterocycl. Chem. 2002, 39, 1035-1038
24. Elghamry, I. Synthesis 2003, 2301-2303
25. Benary, E.; Meyer, H.; Charisius, K. Ber. Dtsch. Chem. Ges. A/B 1926, 59, 108-112
26. Kelber, C.; Schwarz, A. Ber. Dtsch. Chem. Ges. A/B 1912, 45, 2484-2489
27. Petrov, A. A.; Esakov, S. M.; Ershov, B. A. J. Org. Chem. USSR (Eng. Transl.) 1980, 16, 1335-1340
28. Kaushal, R.; Sovani, S.; Deshpande, S. S. J. Indian Chem. Soc. 1942, 19, 107-116
29. Hanson, R. W. J. Chem. Educ. 1997, 74, 430-431
30. Liu, X.; Lu, G.; Guo, Y.; Guo, Y.; Wang, Y.; Wang, X. J. Mol. Catal. A: Chem. 2006, 252, 176-180
31. Keiboom, A. P. G.; De Kreuk, J. F.; van Bekkum, H. J. J. Catal. 1971, 20, 58-66
32. Ram, S.; Ehrenkaufer, R. E. Synthesis 1988, 91-95
33. Kawada, M.; Kashiwagi, M.; Koito, K. Positively-working photoresist using phenolic resin and quinonediazide. Japanese Patent 04301849, 26 Oct, 1992.
34. Tanaka, A.; Arai, Y.; Kim, S. N.; Ham, J.; Usuki, T. J. Asian Nat. Prod. Res. 2011, 13, 290-296
35. Morikawa, A.; Kakimoto, M.; Imai, Y. Macromolecules 1993, 26, 6324-6329
36. Horning, E. C.; Parker, J. A. J. Am. Chem. Soc. 1952, 74, 3870-3872
37. Shimp, D. A.; Ising, S. J.; Christenson, J. R. Cyanate Esters -A New Family of High Temperature Thermosetting Resins. In High Temperature Polymers and Their Uses; Society of Plastics Engineers: Cleveland, OH, 1989; pp 127-140.
38. Jankovic, B. Thermochim. Acta 2011, 519, 114-124
39. Yu, H.; Shen, C. J.; Tian, M. Z.; Qu, J.; Wang, Z. G. Macromolecules 2012, 45, 5140-5150
40. Hamerton, I.; Glynn, S.; Hay, J. N.; Pullinger, M. A.; Shaw, S. J. Polym. Degrad. Stab. 2012, 97, 679-689
41. Ryu, B. Y.; Emrick, T. Macromolecules 2011, 44, 5693-5700
42. Ramirez, M. L.; Walters, R. N.; Savitski, E. P.; Lyon, R. E. Thermal Decomposition of Cyanate Ester Resins; DOT/FAA/AR-01/32; Federal Aviation Administration: Atlantic City, NJ, 2001.
43. Simon, S. L.; Gillham, J. K. J. Appl. Polym. Sci. 1993, 47, 461-485
44. Sheng, X.; Akinc, M.; Kessler, M. R. J. Therm. Anal. Calorim. 2008, 93, 77-85
45. Guenthner, A. J.; Lamison, K. R.; Yandek, G. R.; Masurat, K. C.; Reams, J. T.; Cambrea, L. R.; Mabry, J. M. Role of concurrent chemical and physical processes in determining the maximum use temperatures of thermosetting polymers for aerospace applications. In Abstr. Pap. Am. Chem. Soc. 2011, (243rd ACS National Meeting & Exposition, Denver, CO, 2011), POLY-262.
46. Shimp, D. A.; Ising, S. J. Am. Chem. Soc.: Polym. Mater. Sci. Eng. Prepr. 1992, 66, 504
47. Kamal, M. R.; Sourour, S. Polym. Eng. Sci. 1973, 13, 59-64
48. Kenny, J. M. J. Appl. Polym. Sci. 1994, 51, 761-764
49. Crawford, A. O.; Hamerton, I.; Cavalli, G.; Howlin, B. J. PLoS One 2012, 7, ee44487
50. Crawford, A. O.; Howlin, B. J.; Cavalli, G.; Hamerton, I. React. Funct. Polym. 2012, 72, 596-605
51. Guenthner, A. J.; Lamison, K. R.; Vij, V.; Reams, J. T.; Yandek, G. R.; Mabry, J. M. Macromolecules 2012, 45, 211-220
52. Cambrea, L. R.; Davis, M. C.; Groshens, T. J.; Guenthner, A. J.; Lamison, K. R.; Mabry, J. M. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 4547-4554
53. Dorfman, L.; Furlenmeier, A.; Huebner, C. F.; Lucas, R.; MacPhillamy, H. B.; Mueller, J. M.; Schlittler, E.; Schwyzer, R.; St. André, A. F. Helv. Chim. Acta 1954, 37, 59-75
54. Calandra, J. C.; Svarz, J. J. J. Am. Chem. Soc. 1950, 72, 1027-1028
55. Shimp, D. A. Blend of tris(cyanatophenyl)alkane and bis(cyanatophenyl) alkane. U.S. Patent 4,709,008, 24 Nov, 1987.
56. Guenthner, A. J.; Yandek, G. R.; Mabry, J. M.; Lamison, K. R.; Vij, V.; Davis, M. C.; Cambrea, L. R. Insights into moisture uptake and processability from new cyanate ester monomer and blend studies. In SAMPE International Technical Conference; SAMPE International Business Office: Salt Lake City, UT, 2010; Vol. 55, p 42ISTC-119.
57. Lamison, K. R.; Guenthner, A. J.; Vij, V.; Mabry, J. M. Am. Chem. Soc.: Polym. Mater. Sci. Eng. Prepr. 2011, 104, 299-300