Methylol-functional benzoxazines as precursors for high-performance thermoset polymers: Unique simultaneous addition and condensation polymerization behavior

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 50, Issue 11, 2012, Pages 2275-2285

  Baqar, Mohamed ^a   Agag, Tarek ^a   Ishida, Hatsuo ^a   Qutubuddin, Syed ^a  

^a Case Western Reserve University   (United States)

Author keywords

benzoxazine resin; combined molecular structure; crosslinking; methylol groups; phenols; resins; resole; structure property relations; thermal properties; thermogravimetric analysis (TGA)

Indexed keywords

AROMATIC AMINES; BENZOXAZINE; BENZOXAZINE MONOMERS; BENZOXAZINE RESIN; CROSS-LINKED POLYMERS; DIAMINODIPHENYLMETHANE; EXOTHERMIC PEAKS; FOURIER TRANSFORM INFRARED SPECTRA; HIGH PURITY; HIGH-PERFORMANCE RESINS; HIGH-PERFORMANCE THERMOSETS; HIGH-T; METHYLENE DIANILINE; METHYLOL; OXYDIANILINE; PARAFORMALDEHYDES; PHENOLICS; RESOLE; STRUCTURE PROPERTY RELATION;

ACETAL RESINS; AMINES; CONDENSATION REACTIONS; CROSSLINKING; ETHERS; MOLECULAR STRUCTURE; MONOMERS; PHENOLS; POLYCONDENSATION; RESINS; THERMODYNAMIC PROPERTIES; THERMOGRAVIMETRIC ANALYSIS; THERMOSETS;

POLYMERS;

EID: 84860324913     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.26008     Document Type: Article

References (46)

1. Gardziella, L.,;, Pilato, L. A.,;, Knop, A., Phenolic Resins: Chemistry, Applications, Standardization, Safety and Ecology; Springer: Berlin, 2000; Chapter 6, pp 122-468.
2. Lorenz, L. F.,;, Christiansen, A. W., Ind. Eng. Chem. Res. 1996, 34, 4520-4523.
3. Gibson, S. L.,;, Riffle, J. S., In Synthetic Methods in Step-Growth Polymers;, Rogers, M.,;, Long, T., Eds.; Wiley: New Jersey, 2003; Chapter 7, pp 375-430.
4. Ishida, H., In Handbook of Benzoxazine Resins;, Ishida, H.,;, Agag, T., Eds.; Elsevier: Amsterdam, 2011; Chapter 1, pp 3-81.
5. Ghosh, N.,;, Kiskan, B.,;, Yagci, Y., Prog. Polym. Sci. 2007, 32, 1344-1391.
6. Wang, C. F.,;, Su, Y. C.,;, Kuo, S. W.,;, Huang, C. F.,;, Sheen, Y. C.,;, Chang, F. C., Angew. Chem. Int. Ed. Engl. 2006, 45, 2248-2251.
7. Yagci, Y.,;, Kiskan, B.,;, Ghosh, N. N., J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 5565-5576.
8. Qu, L.,;, Xin, Z., Langmuir 2011, 27, 8365-8370.
9. Sawaryn, C.,;, Landfester, K.,;, Taden, A., Macromolecules 2011, 44, 5650-5658.
10. Liao, C. S.,;, Wang, C. F.,;, Lin, H. C.,;, Chou, H. Y.,;, Chang, F. C., Langmuir 2009, 25, 3359-3362.
11. Goward, G. R.,;, Sebastiani, D.,;, Schnell, I.,;, Spiess, H. W.,;, Kim, H. D.,;, Ishida, H., J. Am. Chem. Soc. 2003, 125, 5792-5800.
12. Kim, H. D.,;, Ishida, H., Macromolecules 2003, 36, 8320-8329.
13. Su, Y. C.,;, Kuo, S. W.,;, Yei, D. R.,;, Xu, H.,;, Chang, F. C., Polymer 2003, 44, 2187-2191.
14. Schnell, I.,;, Brown, S. P.,;, Low, H. Y.,;, Ishida, H.,;, Spiess, H. W., J. Am. Chem. Soc. 1998, 120, 11784-11795.
15. Liu, C.,;, Shen, D.,;, Sebastian, R. M.,;, Marquet, J.,;, Schönfeld, R., Macromolecules 2011, 44, 4616-4622.
16. Chernykh, A.,;, Agag, T.,;, Ishida, H., Macromolecules 2009, 42, 5121-5127.
17. Velez-Herrera, P.,;, Doyama, K.,;, Abe, H.,;, Ishida, H., Macromolecules 2008, 41, 9704-9714.
18. Kiskan, B.,;, Demiray, G.,;, Yagci, Y., J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 3512-3518.
19. Agag, T.,;, Takeichi, T., High Perform. Polym. 2001, 13, S327-S342.
20. Agag, T.,;, Takeichi, T., Macromolecules 2001, 34, 7257-7263.
21. Agag, T.,;, Takeichi, T., Macromolecules 2003, 36, 6010-6017.
22. Kim, H. J.,;, Brunovska, Z.,;, Ishida, H., Polymer 1999, 40, 1815-1822.
23. Brunovska, Z.,;, Ishida, H., J. Appl. Polym. Sci. 1999, 73, 2937-2949.
24. Liu, Y. L.,;, Chou, C. I., J. Polym. Sci. Part A: Polym. Chem. 2005, 43, 5267-5282.
25. Rimdusit, S.,;, Jongvisuttisun, P.,;, Jubsilp, C.,;, Tanthapanihakoon, W., J. Appl. Polym. Sci. 2009, 111, 1225-1234.
26. Ishida, H.,;, Ohba, S., Polymer 2005, 46, 5588-5595.
27. Jin, L.,;, Agag, T.,;, Ishida, H., Eur. Polym. J. 2010, 46, 354-363.
28. Jin, L.,;, Agag, T.,;, Yagci, Y.,;, Ishida, H., Macromolecules 2011, 44, 767-772.
29. Koz, B.,;, Kiskan, B.,;, Yagci, Y., Polym. Bull. 2011, 66, 165-174.
30. Baqar, M.,;, Agag, T.,;, Ishida, H.,;, Qutubuddin, S., Polymer 2011, 52, 307-317.
31. Agag, T.,;, Jin, L.,;, Ishida, H., Polymer 2009, 50, 5940-5944.
32. Dunkers, J.,;, Ishida, H., Spectrochim. Acta A 1995, 51, 1061-1074.
33. Holopainen, T.,;, Alvila, L.,;, Rainio, J.,;, Pakkanen, T. T., J. Appl. Polym. Sci. 1998, 69, 2175-2185.
34. Holopainen, H.,;, Alvila, L.,;, Pakkanen, T. T.,;, Rainio, J., J. Appl. Polym. Sci. 2003, 89, 3582-3586.
35. Nair, C. P. R.,;, Bindu, R. L.,;, Ninan, K. N., J. Appl. Polym. Sci. 2001, 81, 3371-3377.
36. Zhou, D. P.,;, Du, S.,;, Yu, L.,;, Liu, Z., J. Appl. Polym. Sci. 2011, 121, 1938-1945.
37. Douglas, A.,;, Ishida, H., Polymer 2009, 50, 613-626.
38. Gabilondo, N.,;, Larranaga, M.,;, Pena, C.,;, Corcuera, M. A.,;, Echeverría, J. M.,;, Mondragon, I., J. Appl. Polym. Sci. 2006, 102, 2623-2631.
39. Kiskan, B.,;, Koz, B.,;, Yagci, Y., J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 6955-6961.
40. Lin, C. H.,;, Chang, S. L.,;, Hsieh, C. W.,;, Lee, H. H., Polymer 2008, 49, 1220-1229.
41. Wu, X.,;, Zhou, Y.,;, Liu, S. Z.,;, Guo, Y. N.,;, Qiu, J. J.,;, Liu, C. M., Polymer 2011, 52, 1004-1012.
42. Kaushik, A.,;, Singh, P.,;, Verma, G.,;, Rekha, J., Thermoplast. Compos. Mater. 2010, 23, 79-97.
43. Chiu, H. T.,;, Cheng, J. O., Polym. Plast. Technol. Eng. 2007, 46, 801-810.
44. Lin, M. S.,;, Chiu, C. C., J. Appl. Polym. Sci. 2001, 80, 963-969.
45. Kim, M. G.,;, Nieh, W. L., Ind. Eng. Chem. Res. 1991, 30, 1151-1157.
46. Riess, G.,;, Schwob, J. M.,;, Guth, G.,;, Roche, M.,;, Lande, B., In Advances in Polymer Synthesis;, Culbertson, B. M.,;, McGrath, J. E., Eds.; Plenum: New York, 1985; pp 27-49.