Structurally diverse benzoxazines: Synthesis, polymerization, and thermal stability

Designed Monomers and Polymers

Volumn 17, Issue 1, 2014, Pages 47-57

  Vijayakumar, C T ^a   Shamim Rishwana, S ^a   Surender, R ^a   David Mathan, N ^b   Vinayagamoorthi, S ^a   Alam, S ^c  

^a KAMARAJ COLLEGE OF ENGINEERING AND TECHNOLOGY   (India)

^b Nadar Saraswathi College of Engineering and Technology   (India)

^c DEFENCE MATERIALS AND STORES RESEARCH AND DEVELOPMENT ESTABLISHMENT   (India)

Author keywords

Benzoxazine; Bisphenol A; Differential scanning calorimetry; Thermogravimetry

Indexed keywords

BENZOXAZINE; BISPHENOL A; DIFFERENTIAL SCANNING CALORIMETERS; HIGH TEMPERATURE; LOWER TEMPERATURES; PARAFORMALDEHYDES; STRUCTURAL CHARACTERIZATION; SYNTHESIZED MATERIALS;

ACETAL RESINS; AROMATIZATION; CURING; DIFFERENTIAL SCANNING CALORIMETRY; GLASS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMER BLENDS; THERMODYNAMIC STABILITY; THERMOGRAVIMETRIC ANALYSIS;

PHENOLS;

EID: 84886098456     PISSN: 1385772X     EISSN: 15685551     Source Type: Journal    
DOI: 10.1080/15685551.2013.797216     Document Type: Article

References (40)

1. Ishida H, Rodriguez Y. Curing kinetics of a new benzoxazine- based resin by differential scanning calorimetry. Polymer. 1995;36: 3151-3358.
2. Takeichi T, Nakamura K, Agag T, Muto H. Synthesis of cresol-based benzoxazine monomers containing allyl groups and the properties of the polymers therefrom. Des. Monomers Polym. 2004;7: 727-740.
3. Ghosh NN, Kiskan B, Yagci Y. Polybenzoxazines - new high performance thermosetting resins: synthesis and properties. Prog. Polym. Sci. 2007;32: 1344-1391.
4. Holly FW, Cope AC. Condensation product of aldehydes and ketones with o-aminobenzyl alcohol and o-hydroxybenzylamine. J. Am. Chem. Soc. 1944;66: 1875-1879.
5. Riess G, Schwob JM, Guth G, Roche M, Lande B. Ring opening polymerization of benzoxazines. In: Culbertson BM, McGrath JE, editors. Advances in polymer synthesis. New York (NY): Plenum; 1985. 27-49.
6. Higginbottom HP, Drumm MF, Process for deposition of resin dispersions on metal substrates. United States patent US, 4557979. 1985 Dec 10.
7. Liu J, Ishida H. A new class of phenolic resins with ring opening polymerisation. In: Salamone JC, editor. The polymeric materials encyclopedia. Boca Raton (FL): CRC press; 1996. 484-494.
8. Kisksan B, Dogan F, Durmaz YY, Yagci Y. Synthesis, characterization and thermally-activated curing of azobenzene- containing benzoxazines. Des. Monomers Polym. 2008;11: 473-482.
9. Reghunadhan Nair CP. Advances in addition cure - phenolic resins. Des. Monomers Polym. 2004;29: 401-498.
10. Yagci Y, Kiskan B, Ghosh NN. Recent advancement on polybenzoxazine - a newly developed high performance thermoset. J. Polym. Sci. Part A: Polym. Chem. 2009;47: 5565-5576.
11. Cao H, Yan D, Sun X, Xu R, Yu D. Synthesis and characterization of a novel 2-oxazoline-benzoxazine compound with incorporated polyhedral oligomeric silsequioxane. Des. Monomers Polym. 2009;12: 556-578.
12. Ishida H, Low HY. A study on the volumetric expansion of benzoxazine-based phenolic resin. Macromolecules. 1997;30: 1099-1106.
13. Kim HD, Ishida H. Study on the chemical stability of benzoxazine-based phenolic resins in carboxylic acids. J. Appl. Polym. Sci. 2001;79: 1207-1219.
14. Santhosh Kumar KS, Regunathan Nair CP, Sadhana R, Ninan KN. Benzoxazine-bismaleimide blends: curing and thermal properties. Eur. Polymer J. 2007;43: 5084-5096.
15. Kukut M, Kiskan B, Yagci Y. Self-curable benzoxazine functional polybutadienes synthesized by click chemistry. Des. Monomers Polym. 2009;12: 167-176.
16. Ishida H. Process for preparation of benzoxazine compounds in solventless systems, United States patent US, 5,543,516. 1996 Aug 6.
17. Cao HW, Xu RW, Liu H, Yu DS. Mannich reaction of phenolphthalein and synthesis of a novel polybenzoxazine. Des. Monomers Polym. 2006;9: 369-382.
18. Chen KC, Li HT, Chen WB, Laio CH, Sun KW, Chih Chang FC. Synthesis and characterization of novel siloxane-imide-containing polybenzoxazine. Polym. Int. 2011;60: 436-442.
19. Santhosh Kumar KS, Reghunadhan Nair CP, Ninan KN, Kulkarni AD, Wadgaonkar PP. Synthesis and properties of new polybenzoxazines containing (substituted) cyclohexyl moieties. Polym. Adv. Technol. 2009;20: 1107-1113.
20. Dansiri N, Yanumet N, Ellis JW, Ishida H. Resin transfer molding of natural fiber reinforced polybenzoxazine composities. Polym. Compos. 2002;23: 352-360.
21. Chan KP, Cristo PL, McGrath PM, Method for preparing high purity indane bisphenols. United States patent US, 5, 994,596. 1999 Nov 30.
22. Faler GR, Lynch JC, Substantially pure spirobiindane bisphenols and method for their preparation. United State patent US. 4, 791,234. 1988 Dec 13.
23. Agag T, Takeichi T. Novel benzoxazine monomers containing p-phenyl propargyl ether: polymerization of monomers and properties of polybenzoxazines. Macromolecules 2001;34: 7257-7263.
24. Agag T, Takeichi T. Synthesis and characterization of novel benzoxazine monomers containing allyl groups and their high performance thermosets. Macromolecules 2003;36: 6010-6017.
25. Brunovska Z, Liu JP, Ishida H. 1,3,5-Triphenylhexahydro- 1,3,5-triazine active intermediate and precursor in the novel synthesis of benzoxazine monomers and oligomers. Macromol. Chem. Phys. 1999;200: 1745-1752.
26. Dunkers J, Ishida H. Vibrational assignments of N, N-bis (3,5-dimethyl-2-hydroxybenzyl)methylamine in the fingerprint region. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 1995;51: 855-867.
27. Liu J, Agag T, Ishida H. Main-chain benzoxazine oligomers: a new approach for resin transfer moldable neat benzoxazines for high performance application. Polymer 2010;51: 5688-5694.
28. Ning X, Ishida H. Phenolic materials viaring-opening polymerisation: synthesis and characterization of bisphenol- A based benzoxazines and their polymers. J. Polym. Sci. Part A: Polym. Chem. 1994;32: 1121-1129.
29. Lochab B, Varma IK, Bijwe J. Thermal behaviour of cardanol- based benzoxazines monomers and polymers. J. Therm. Anal. Calorim. 2010;102: 769-774.
30. Ishida H, Sanders DP. Regioselectivity and network structure of difunctional alkyl-substituted aromatic amine-based polybenzoxazines. Macromolecules. 2000;33: 8149-8157.
31. Low HY, Ishida H. Structural effects of phenols on the thermal and thermo-oxidative degradation of polybenzoxazines. Polymer. 1999;40: 4365-4376.
32. Low HY, Ishida H. An investigation of the thermal and thermo-oxidative degradation of polybenzoxzines with a reactive functional group. J. Polym. Sci. Part B: Polym. Phys. 1999;37: 647-659.
33. Kim HJ, Brunovska Z, Ishida H. Synthesis and thermal characterization of polybenzoxazines based on acetylenefunctional monomers. Polymer. 1999;40: 6565-6573.
34. Kim HJ, Brunovska Z, Ishida H. Molecular characterization of the polymerization of acetylene-functional benzoxazine resins. Polymer. 1999;40: 1815-1822.
35. Kim HJ, Brunovska Z, Ishida H. Dynamic mechanical analysis on highly thermally stable polybenzoxazines with an acetylene functional group. J. Appl. Polym. Sci. 1999;73: 857-862.
36. Brunovska Z, Lyon R, Ishida H. Thermal properties of phthalonitrile functional polybenzoxazines. Thermochim. Acta. 2000;357: 195-203.
37. Brunovska Z, Ishida H. Thermal study on copolymers of phthalonitrile and phenylnitrile-functional benzoxazines. J. Appl. Polym. Sci. 1999;73: 2937-2949.
38. Ishida H, Sanders DP. Improved thermal and mechanical properties of polybenzoxazines based on alkyl-substituted aromatic amine. J. Polym. Sci. Part B: Polym. Phys. 2000;38: 3289-3301.
39. Wang YX, Ishida H. Synthesis and properties of new thermoplastic polymers from substituted 3,4- dihydro-2H-1,3-benzoxazines. Macromolecules. 2000;33: 2839-2847.
40. Chirachanchai S, Laobuthee A, Phongtamruga S. Self termination of ring opening reaction of p-substituted phenol-based benzoxazines: an obstructive effect via intramolecular hydrogen bond. J. Heterocycl. Chem. 2009;46: 714-721.