Catalytic opening of lateral benzoxazine rings by thiols

Handbook of Benzoxazine Resins

Volumn , Issue , 2011, Pages 211-234

  Gorodisher, Ilya ^a   DeVoe, Robert J ^a   Webb, Robert J ^a  

^a 3M COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84865648124     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-444-53790-4.00056-4     Document Type: Chapter

References (28)

1. Ghosh N.N., Kiskan B., Yagci Y. Polybenzoxazines-New high performance thermosetting resins: synthesis and properties. Prog. Polym. Sci. 2007, 32:1344-1391.
2. Li Y.T., Tietze R., Chaudhari M. Innovations in polybenzoxazines and their commercial status. ACS Polym. Mat. Sci. Eng. Preprints 2010, 102:740.
3. Yildirim A., Kiskan B., Demirel A.L., Yagci Y. Synthesis, characterization and properties of naphthoxazine-functional poly(propyleneoxide)s. Eur. Poly. J. 2006, 42:3006-3014.
4. Allen D.J., Ishida H. Physical and mechanical properties of flexible polybenzoxazine resins: Effect of aliphatic diamine chain length. J. Appl. Polym. Sci. 2006, 101:2798-2809.
5. Allen D.J., Ishida H. Polymerization of linear aliphatic diamine-based benzoxazine resins under inert and oxidative environments. Polymer 2007, 48:6763-6772.
6. Allen D.J., Ishida H. Effect of phenol substitution on the network structure and properties of linear aliphatic diamine based benzoxazines. Polymer 2009, 50:613-626.
7. Minigher A., Benedetti E., DeCiacomo O., Campaner P., Aroulmoji V. Synthesis and characterization of novel cardanol based benzoxazines. Nat. Prod. Commun. 2009, 4:521-528.
8. Takeichi T., Kano T., Agag T. Synthesis and thermal cure of high molecular weight polybenzoxazine precursors and the properties of the thermosets. Polymer 2005, 46:12172-12180.
9. Agag T., Takeichi T. High molecular weight AB-type benzoxazines as new precursors for high-performance thermosets. J. Polym. Sci. A Polym. Chem. 2007, 45:1878-1888.
10. Kiskan B., Yagci Y., Ishida H. Synthesis, characterization and properties of new thermally curable polyetheresters containing benzoxazine moieties in the main chain. J. Polym. Sci. A Polym. Chem. 2008, 46:414-420.
11. Chaisuwan T., Komalwanich T., Luangsukrerk S., Wongkasemjit S. Removal of heavy metals from model wastewater by using polybenzoxazine aerogel. Desalination 2010, 256:108-114.
12. Sawaryn C., Landfester K., Taden A. Benzoxazine miniemulsions stabilized with polymerizable nonionic benzoxazine surfactants. Macromolecules 2010, 43:8933-8941.
13. Tuzun A., Kiskan B., Alemdar N., Erciyes A.T., Yagci Y. Benzoxazine containing polyester thermosets with improved adhesion and flexibility. J. Polym. Sci. A Polym. Chem. 2010, 48:4279-4284.
14. Baqar M., Agag T., Ishida H., Qutubuddin S. Poly(benzoxazine-co-urethane)s: a new concept for phenolic/urethane copolymers via one-pot method. Polymer 2011, 52:307-317.
15. Koz B., Kiskan B., Yagci Y. A novel benzoxazine monomer with methacrylate functionality and its thermally curable (co)polymers. Polym. Bull. 2011, 66:165-174.
16. Ishida H., Wang Y.X. Cationic ring-opening polymerization of benzoxazines. Polymer 1999, 40(16):4563-4570.
17. I. Gorodisher, WO 2011025652A1.
18. March J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure 1985, 605-606. Wiley, New York. third ed.
19. Kende A.S., Curran D.P. Regiochemical control in dihydrophenanthrene synthesis. A photochemical total synthesis of juncusol. J. Am. Chem. Soc. 1979, 101:1857-1864.
20. Boger D.L., Mullican M.D. Regiospecific total synthesis of juncusol. J. Org. Chem. 1984, 49:4045-4050.
21. Hase A.H., Wähälä K. e-EROS Encyclopedia of Reagents for Organic Synthesis 2001, 2118-2129. John Wiley and Sons, New York.
22. Bax A., Summers M.F. Proton and carbon-13 assignments from sensitivity-enhanced detection of heteronuclear multiple-bond connectivity by 2D multiple quantum NMR. J. Am. Chem. Soc. 1986, 108:2093-2094.
23. Hurd R.E., John B.K. Gradient-enhanced proton-detected heteronuclear multiple-quantum coherence spectroscopy. J. Magn. Reson. 1991, 91:648-653.
24. March J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure 1985, 221-235. Wiley, New York. third ed.
25. Johnson E.C.B., Kent S. Insights into the mechanism and catalysis of the native chemical ligation reaction. J. Am. Chem. Soc. 2006, 128:6640-6646.
26. Kemp D.S., Vellaccio F. Organic Chemistry 1980, 701. Worth Publishing, London.
27. Crampton M.R., Willison M.J. Some studies of substituent effects on the nucleophilic reactivities of thiophenoxide ions. J. Chem. Soc. Perkin Trans. 1974, 2:238-241.
28. Gorodisher I. Novel Polymers and Organics for Optical Second Harmonic Generation. Ph.D. Thesis June 1990, 38. Massachusetts Institute of Technology, Cambridge, MA.