Synthesis, thermal properties and curing kinetics of fluorene diamine-based benzoxazine containing ester groups

European Polymer Journal

Volumn 49, Issue 9, 2013, Pages 2759-2768

  He, Xuan Yu ^a   Wang, Jun ^a   Wang, Yu Dan ^a   Liu, Chen Juan ^a   Liu, Wen Bin ^a   Yang, Lei ^b  

^a HARBIN ENGINEERING UNIVERSITY   (China)

^b NORTHEAST FORESTRY UNIVERSITY   (China)

Author keywords

Curing kinetics; Fluorene diamine based benzoxazine; Polymerization behavior; Thermal properties

Indexed keywords

BENZOXAZINE; BENZOXAZINE MONOMERS; CURING KINETICS; D. DYNAMIC MECHANICAL THERMAL ANALYSES (DMTA); FOURIER TRANSFORM INFRA REDS; MACROMOLECULAR BACKBONE; POLYMERIZATION BEHAVIOR; THERMAL AND MECHANICAL PROPERTIES;

ACETAL RESINS; AMINES; CURING; DIFFERENTIAL SCANNING CALORIMETRY; ESTERIFICATION; ESTERS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MECHANICAL PROPERTIES; MONOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; POLYMER BLENDS; POLYMERIZATION; SYNTHESIS (CHEMICAL); THERMOANALYSIS; THERMODYNAMIC PROPERTIES; THERMOGRAVIMETRIC ANALYSIS;

KINETICS;

EID: 84881367410     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2013.06.018     Document Type: Article

References (65)

1. X. Ning, and H. Ishida Phenolic materials via ring-opening polymerization: synthesis and characterization of bisphenol-A based benzoxazines and their polymers J Polym Sci Part A: Polym Chem 32 1994 1121 1129
2. X. Ning, and H. Ishida Phenolic materials via ring-opening polymerization of benzoxazines: effect of molecular structure on mechanical and dynamic mechanical properties J Polym Sci Part B: Polym Phys 32 1994 921 927
3. H. Ishida, and D.J. Allen Physical and mechanical characterization of near-zero shrinkage polybenzoxazines J Polym Sci Part B: Polym Phys 34 1996 1019 1030
4. A. Laobuthee, S. Chirachanchai, H. Ishida, and K. Tashiro Asymmetric mono-oxazine: an inevitable product from Mannich reaction of benzoxazine dimers J Am Chem Soc 123 2001 9947 9955
5. N.N. Ghosh, B. Kiskan, and Y. Yagci Polybenzoxazines - New high performance thermosetting resins: synthesis and properties Prog Polym Sci 32 2007 1344 1391
6. M. Spontón, G. Lligadas, J.C. Ronda, M. Galià, and V. Cádiz Development of a DOPO-containing benzoxazine and its high-performance flame retardant copolybenzoxazines Polym Degrad Stabil 94 2009 1693 1699
7. T. Agag, and T. Takeichi Novel benzoxazine monomers containing p-phenyl propargyl ether: polymerization of monomers and properties of polybenzoxazines Macromolecules 34 2001 7257 7263
8. T. Agag, and T. Takeichi Synthesis and characterization of novel benzoxazine monomers containing allyl groups and their high performance thermosets Macromolecules 36 2003 6010 6017
9. Y.C. Su, and F.C. Chang Synthesis and characterization of fluorinated polybenzoxazine material with low dielectric constant Polymer 44 2003 7989 7996
10. H. Ishida, and S. Ohba Synthesis and characterization of maleimide and norbornene functionalized benzoxazines Polymer 46 2005 5588 5595
11. H.C. Liu, W.C. Su, and Y.L. Liu Self-assembled benzoxazine-bridged polysilsesquioxanes exhibiting ultralow-dielectric constants and yellow-light photoluminescent emission J Mater Chem 21 2011 7182 7187
12. A.W. Kawaguchi, A. Sudo, and T. Endo Synthesis of highly polymerizable 1,3-benzoxazine assisted by phenyl thio ether and hydroxyl moieties J Polym Sci Part A: Polym Chem 50 2012 1457 1461
13. C. Zúñiga, G. Lligadas, J.C. Ronda, M. Galià, and V. Cádiz Self-foaming diphenolic acid benzoxazine Polymer 53 2012 3089 3095
14. D.J. Allen, and H. Ishida Effect of phenol substitution on the network structure and properties of linear aliphatic diamine-based benzoxazines Polymer 50 2009 613 626
15. D.J. Allen, and H. Ishida Polymerization of linear aliphatic diamine-based benzoxazine resins under inert and oxidative environments Polymer 48 2007 6763 6772
16. C.H. Lin, S.L. Chang, C.W. Hsieh, and H.H. Lee Aromatic diamine-based benzoxazines and their high performance thermosets Polymer 49 2008 1220 1229
17. C.H. Lin, H.T. Lin, J.W. Sie, K.Y. Hwang, and A.P. Tu Facile, one-pot synthesis of aromatic diamine-based phosphinated benzoxazines and their flame-retardant thermosets J Polym Sci Part A: Polym Chem 48 2010 4555 4566
18. S.L. Chang, and C.H. Lin Facile, one-pot synthesis of aromatic diamine-based benzoxazines and their advantages over diamines as epoxy hardeners J Polym Sci Part A: Polym Chem 48 2010 2430 2437
19. T. Agag, L. Jin, and H. Ishida A new synthetic approach for difficult benzoxazines: Preparation and polymerization of 4,4′-diaminodiphenyl sulfone-based benzoxazine monomer Polymer 50 2009 5940 5944
20. M. Spontón, M.S. Larrechi, J.C. Ronda, M. Galià, and V. Cádiz Synthesis and study of the thermal crosslinking of bis(m-aminophenyl) methylphosphine oxide based benzoxazine J Polym Sci Part A: Polym Chem 46 2008 7162 7172
21. A. Chernykh, T. Agag, and H. Ishida Novel benzoxazine monomer containing diacetylene linkage: an approach to benzoxazine thermosets with low polymerization temperature without added initiators or catalysts Polymer 50 2009 3153 3157
22. W.W. Men, Z.J. Lu, and Z.R. Zhan Synthesis of a novel benzoxazine precursor containing phenol hydroxyl groups and its polymer J Appl Polym Sci 109 2008 2219 2223
23. C.H. Lin, S.L. Chang, H.H. Lee, H.C. Chang, K.Y. Hwang, and A.P. Tu Fluorinated benzoxazines and the structure-property relationship of resulting polybenzoxazines J Polym Sci Part A: Polym Chem 46 2008 4970 4983
24. Y.L. Liu, C.W. Hsu, and C.I. Chou Silicon-containing benzoxazines and their polymers: copolymerization and copolymer properties J Polym Sci Part A: Polym Chem 45 2007 1007 1015
25. P. Yang, and Y. Gu A novel benzimidazole moiety-containing benzoxazine: synthesis, polymerization, and thermal properties J Polym Sci Part A: Polym Chem 50 2012 1261 1271
26. S. Rimdusit, S. Tiptipakorn, C. Jubsilp, and T. Takeichi Polybenzoxazine alloys and blends: some unique properties and applications React Funct Polym 73 2013 369 380
27. M. Fakis, F. Zacharatos, V. Gianneta, P. Persephonis, V. Giannetas, and A. Nassiopoulou Photoluminescence properties of porous silicon/fluorene dye composites Mater Sci Eng B 165 2009 252 255
28. S.C. Lin, and E.M. Pearce Epoxy resins. II. The preparation, characterization, and curing of epoxy resins and their copolymers J Polym Sci: Polym Chem Ed 17 1979 3095 3119
29. W. Liu, Q. Qiu, J. Wang, Z. Huo, and H. Sun Curing kinetics and properties of epoxy resin-fluorenyl diamine systems Polymer 49 2008 4399 4405
30. T.A. Reddy, and M. Srinivasan Preparation and properties of cardopolyimides containing phenoxaphosphine units J Polym Sci Part A: Polym Chem 27 1989 1419 1424
31. S.H. Hsiao, and C.T. Li Synthesis and characterization of new fluorene-based poly(ether imide)s J Polym Sci Part A: Polym Chem 37 1999 1403 1412
32. A.D. Sagar, R.D. Shingte, P.P. Wadgaonkar, and M.M. Salunkhe Polyamides containing s-triazine rings and fluorene "cardo"groups: synthesis and characterization Eur Polym J 37 2001 1493 1498
33. M. Nishikawa Design of polyimides for liquid crystal alignment films Polym Advan Technol 11 2000 404 412
34. P.R. Srinivasan, V. Mahadevan, and M. Srinivasan Preparation and properties of some cardopolyamides J Polym Sci: Polym Chem Ed 19 1981 2275 2285
35. J. Wang, M.Q. Wu, W.B. Liu, S.W. Yang, J.W. Bai, and Q.Q. Ding Synthesis, curing behavior and thermal properties of fluorene containing benzoxazines Eur Polym J 46 2010 1024 1031
36. Y.L. Liu, C.Y. Chang, C.Y. Hsu, M.C. Tseng, and C.I. Chou Preparation, characterization, and properties of fluorene-containing benzoxazine and its corresponding cross-linked polymer J Polym Sci Part A: Polym Chem 48 2010 4020 4026
37. Y. Lu, M. Li, Y. Zhang, D. Hu, L. Me, and W. Xu Synthesis and curing kinetics of benzoxazine containing fluorene and furan groups Thermochim Acta 515 2011 32 37
38. Z. Fu, H. Liu, H. Cai, X. Liu, G. Ying, and K. Xu Synthesis, thermal polymerization, and properties of benzoxazine resins containing fluorenyl moiety Polym Eng Sci 52 2012 2473 2481
39. H.C. Chang, C.H. Lin, Y.W. Tian, Y.R. Feng, and L.H. Chan Synthesis of 9,9-bis(4-aminophenyl)fluorene-based benzoxazine and properties of its high-performance thermoset J Polym Sci Part A: Polym Chem 50 2012 2201 2210
40. J. Wang, X.Y. He, J.T. Liu, W.B. Liu, and L. Yang Investigation of the polymerization behavior and regioselectivity of fluorene diamine-Based benzoxazines Macromol Chem Phys 214 2013 617 628
41. A. Tuzun, B. Kiskan, N. Alemdar, A.T. Erciyes, and Y. Yagci Benzoxazine containing polyester thermosets with improved adhesion and flexibility J Polym Sci Part A: Polym Chem 48 2010 4279 4284
42. M. Baqar, T. Agag, H. Ishida, and S. Qutubuddin Poly(benzoxazine-co- urethane)s: a new concept for phenolic/urethane copolymers via one-pot method Polymer 52 2011 307 317
43. H. Yeganeh, and A. Jangi Thermally curable polyurethanes containing naphthoxazine groups in the main chain Polym Int 59 2010 1375 1383
44. B. Kiskan, Y. Yagci, and H. Ishida Synthesis, characterization, and properties of new thermally curable polyetheresters containing benzoxazine moieties in the main chain J Polym Sci Part A: Polym Chem 46 2008 414 420
45. C. Jubsilp, T. Takeichi, and S. Rimdusit Property enhancement of polybenzoxazine modified with dianhydride Polym Degrad Stabil 96 2011 1047 1053
46. J. Wang, X. Fang, M.Q. Wu, X.Y. He, W.B. Liu, and X.D. Shen Synthesis, curing kinetics and thermal properties of bisphenol-AP-based benzoxazine Eur Polym J 47 2011 2158 2168
47. H. Ishida, and Y. Rodriguez Curing kinetics of a new benzoxazine-based phenolic resin by differential scanning calorimetry Polymer 36 1995 3151 3158
48. H. Ishida, and Y. Rodriguez Catalyzing the curing reaction of a new benzoxazine-based phenolic resin J Appl Polym Sci 58 1995 1751 1760
49. C. Jubsilp, S. Damrongsakkul, T. Takeichi, and S. Rimdusit Curing kinetics of arylamine-based polyfunctional benzoxazine resins by dynamic differential scanning calorimetry Thermochim Acta 447 2006 131 140
50. Y. Liu, Z. Yue, and J. Gao Synthesis, characterization, and thermally activated polymerization behavior of bisphenol-S/aniline based benzoxazine Polymer 51 2010 3722 3729
51. C. Andronescu, S.A. Garea, C. Deleanu, and H. Iovu Characterization and curing kinetics of new benzoxazine monomer based on aromatic diamines Thermochim Acta 530 2012 42 51
52. W.S. Chow, S. Grishchuk, T. Burkhart, and J. Karger-Kocsis Gelling and curing behaviors of benzoxazine/epoxy formulations containing 4,4′-thiodiphenol accelerator Thermochim Acta 543 2012 172 177
53. L. Ke, D. Hu, Y. Lu, S. Feng, Y. Xie, and W. Xu Copolymerization of maleimide-based benzoxazine with styrene and the curing kinetics of the resultant copolymer Polym Degrad Stabil 97 2012 132 138
54. C. Jubsilp, K. Punson, T. Takeichi, and S. Rimdusit Curing kinetics of benzoxazine-epoxy copolymer investigated by non-isothermal differential scanning calorimetry Polym Degrad Stabil 95 2010 918 924
55. W. Liu, J. Wang, Q. Qiu, L. Ji, C. Wang, and M. Zhang Synthesis and characterisation of 9, 9-bis (4-hydroxyphenyl)-fluorene catalysed by cation exchanger Pigm Resin Technol 37 2008 9 15
56. F. Kasapoglu, I. Cianga, Y. Yagci, and T. Takeichi Photoinitiated cationic polymerization of monofunctional benzoxazine J Polym Sci Part A: Polym Chem 41 2003 3320 3328
57. S. Vyazovkin, A.K. Burnham, J.M. Criado, L.A. Pérez-Maqueda, C. Popescu, and N. Sbirrazzuoli ICTAC kinetics committee recommendations for performing kinetic computations on thermal analysis data Thermochim Acta 520 2011 1 19
58. C. Zhang, W.K. Binienda, L. Zeng, X. Ye, and S. Chen Kinetic study of the novolac resin curing process using model fitting and model-free methods Thermochim Acta 523 2011 63 69
59. S. Vyazovkin Computational aspects of kinetic analysis: Part C. The ICTAC kinetics project - the light at the end of the tunnel? Thermochim Acta 355 2000 155 163
60. S. Vyazovkin, and N. Sbirrazzuoli Isoconversional kinetic analysis of thermally stimulated processes in polymers Macromol Rapid Commun 27 2006 1515 1532
61. J. Wang, H. Wang, J.T. Liu, W.B. Liu, and X.D. Shen Synthesis, curing kinetics and thermal properties of novel difunctional chiral and achiral benzoxazines with double chiral centers J Therm Anal Calorim 2013 10.1007/s10973-013-3081-8
62. M.J. Starink The determination of activation energy from linear heating rate experiments: a comparison of the accuracy of isoconversion methods Thermochim Acta 404 2003 163 176
63. M.R. Kamal, and S. Sourour Kinetics and thermal characterization of thermoset cure Polym Eng Sci 13 1973 59 64
64. F.Y.C. Boey, and W. Qiang Experimental modeling of the cure kinetics of an epoxy-hexaanhydro-4-methylphthalicanhydride (MHHPA) system Polymer 41 2000 2081 2094
65. T.H. Hsieh, and A.C. Su Cure kinetics of an epoxy-novolac molding compound J Appl Polym Sci 41 1990 1271 1280