Use of renewable resource vanillin for the preparation of benzoxazine resin and reactive monomeric surfactant containing oxazine ring

Polymer

Volumn 55, Issue 6, 2014, Pages 1443-1451

  Van, Amy ^a   Chiou, Kevin ^a   Ishida, Hatsuo ^a  

^a Case Western Reserve University   (United States)

Author keywords

Polybenzoxazine; Renewable resource; Vanilin

Indexed keywords

ALDEHYDES; DIFFERENTIAL SCANNING CALORIMETRY; DYNAMIC LIGHT SCATTERING; EMULSIFICATION; EMULSIONS; ETHYLENE; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MONOMERS; NATURAL RESOURCES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYETHYLENE OXIDES; SURFACE ACTIVE AGENTS;

BENZOXAZINE RESIN; EMULSION DROPLETS; FOURIER TRANSFORM INFRA RED (FTIR) SPECTROSCOPY; MONOMERIC SURFACTANTS; POLYBENZOXAZINE; PROTON NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RENEWABLE RESOURCE; VANILIN;

THERMOGRAVIMETRIC ANALYSIS;

EID: 84896400458     PISSN: 00323861     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.polymer.2014.01.041     Document Type: Article

References (74)

1. Overview and historical background of polybenzoxazine research. Chapter 1 H. Ishida, and T. Agag Handbook of polybenzoxazine resins 2011 Elsevier Amsterdam: The Netherlands 3 81
2. B.S. Rao, and A.W. Palamisamy Monofunctional benzoxazine from cardanol for bio-composite applications React Funct Polym 71 2011 148 154
3. P. Kasemsiri, S. Hiziroglu, and S. Rimdusit Properties of wood polymer composites from Eastern Red Cedar particles reinforced with benzoxazine resin/cashew nut shell liquid copolymer Compos Part A 42 2011 1454 1462
4. T. Agag, S.Y. An, and H. Ishida 1,3-Bis(benzoxazine) from cashew nut shell oil and diaminodiphenyl methane and its composites with wood flour J Appl Polym Sci 127 2012 2710 2714
5. H. Ishida, and H.Y. Low Synthesis of benzoxazine functional silane and adhesion properties of glass-fiber-reinforced polybenzoxazine composites J Appl Polym Sci 69 1998 2559 2567
6. S.B. Shen, and H. Ishida Processing and characterization of carbon fiber reinforced polynaphthoxazine composite J Mat Sci 31 1996 5945 5952
7. J.S. Jang, and H. Yang Toughness improvement of carbon-fibre/ polybenzoxazine composites by rubber modification Compos Sci Technol 60 2000 457 463
8. H. Ishida, and T. Chaisuwan Mechanical property improvement of carbon fiber reinforced polybenzoxazine by rubber interlayer Polym Compos 24 2003 597
9. C.L. Xin, X.P. Yang, and D.S. Yu Non-isothermal cure kinetics of polybenzoxazine/carbon fiber composites by phase change theory Polym Polym Compos 13 2005 599 605
10. K.S.S. Kumar, C.P.R. Nair, and K.N. Ninan Effect of fiber length and composition on mechanical properties of carbon fiber-reinforced polybenzoxazine Polym Adv Technol 19 2008 895 904
11. S. Rimdusit, P. Jongvisuttisun, C. Jubsilp, and W. Tanthapanihakoon Highly processable ternary systems based on benzoxazine, epoxy, and phenolic resins for carbon fiber composite processing J Appl Polym Sci 111 2009 1225 1234
12. S. Rimdusit, C. Liengvachiranon, S. Tiptipakom, and C. Jubsilp Thermomechanial characteristics of benzoxazine-urethane copolymers and their carbon fiber-reinforced composites J Appl Polym Sci 113 2009 3823 3830
13. M.A. Nahil, and P.T. Williams Recycling of carbon fibre reinforced polymeric waste for the production of activated carbon fibres J Anal Appl Pyrol 91 2011 67 75
14. K. Qiao, B. Zhu, X.D. Gao, C.R. Di, W. Zhao, and X.Y. Yin A study on the comparison between difference matrices used for carbon fiber reinforced composite core Appl Mech Mater 66-68 2011 1072 1077
15. C. Jubsilp, C. Panyawanitchakun, and S. Rimdusit Flammability and thermomechanical properties of dianhydride-modified polybenzoxazine composites reinforced with carbon fiber Polym Compos 34 2013 2067 2075
16. T. Agag, and T. Takeichi Polybenzoxazine-montmorillonite hybrid nanocomposites: synthesis and characterization Polymer 41 2000 7083 7090
17. P. Phiriyawirut, R. Magaraphan, and H. Ishida Preparation and characterization of polybenzoxazine-clay immiscible nanocomposite Mater Res Innovations 4 2001 187 196
18. C.Y. Wang, and T. Zhao Polynaphthoxazines-montmorillonite nanocomposites: synthesis and characterization Chin Chem Lett 12 2001 935 936
19. T. Agag, T. Takeichi, H. Toda, and T. Kobayashi Epoxy-clay nanocomposites using polybenzoxazine as a curing agent Int J Mater Prod Tech 2 2001 706 711
20. T. Takeichi, R. Zeidam, and T. Agag Polybenzoxazine/clay hybrid nanocomposites: influence of preparation method on the curing behavior and properties of polybenzoxazines Polymer 43 2002 45 53
21. Z. Shi, D.S. Yu, Y. Wang, and R. Xu Nonisothermal cure kinetics in the synthesis of polybenzoxazine-clay nanocomposites J Appl Polym Sci 88 2003 194 200
22. T. Takeichi, and Y. Guo Synthesis and characterization of poly (urethane-benzoxazine)/clay hybrid nanocomposite J Appl Polym Sci 90 2003 4075 4083
23. Z.Y. Ye, and Y. Gu Study on curing of polybenzoxazine/vermiculite nanocomposites Acta Polym Sin 2004 208 212
24. Q. Chen, R.W. Xu, and D.S. Yu Preparation of nanocomposites of thermosetting resin from benzoxazine and bisoxazoline with montmorillonite J Appl Polym Sci 100 2006 4741 4747
25. T. Agag, and T. Takeichi Preparation and cure behavior of organoclay-modified allyl-functional benzoxazine resin and the properties of their nanocomposites Polym Compos 29 2008 750 757
26. H.K. Fu, C.F. Huang, S.W. Kuo, H.C. Lin, D.R. Yei, and F.C. Chang Effect of an organically modified nanoclay on low-surface-energy materials of polybenzoxazine Macromol Rapid Commun 29 2008 1216 1220
27. C.K. Chozhan, M. Alagar, and P. Gnanasundaram Synthesis and characterization of 1,1-bis(3-methyl-4-hydroxy phenyl)-cyclohexane polybenzoxazine-organoclay hybrid nanocomposites Acta Mater 57 2009 782 794
28. S.A. Garea, H. Lovu, A. An. Nicolescu, and C. Deleanu A new strategy for polybenzoxazine-momtmorillonite nanocomposites synthesis Polym Test 28 2009 338 347
29. 2/polybenzoxazine composites J Appl Polym Sci 120 2011 1525 1532
30. 2) hybrid nanocomposites through in situ sol-gel method J Sol-Gel Sci Technol 60 2011 33 40
31. U. Thubsuang, H. Ishida, S. Wongkasemjit, and T. Chaisuwan Novel template confinement derived from polybenzoxazine-based carbon xerogels for synthesis of ZSM-5 nanoparticles via microwave irradiation Microporous Mesoporous Mater 156 2012 7 15
32. H.W. Cui, and S.W. Kuo Nanocomposites of polybenzoxazine and exfoliated montmorillonite uysing a polyhedral oligomeric silsesquioxane surfactant and click chemistry J Polym Res 20 114 2013 1 13
33. Q. Chen, R.W. Xu, and D.S. Yu Multiwalled carbon nanotube/polybenzoxazine nanocomposites: preparation, characterization and properties Polymer 47 2006 7711 7719
34. L. Yang, C. Zhang, S. Pilla, and S. Gong Polybenzoxazine-core shell rubber-carbon nanotube nanocomposites Compos Part A 39 2008 1653 1659
35. J.M. Huang, M.F. Tsai, S.J. Yang, and W.M. Chiu Preparation and thermal properties of multiwalled carbon nanotube/polybenzoxazine nanocomposites J Appl Polym Sci 122 2011 1898 1904
36. Y.H. Liu, B. Wang, and X.L. Jing Thermal properties of hyperbranched polyborate functionalized multiwall carbon nanotube/polybenzoxazine composites Polym Compos 32 2011 1352 1361
37. Y.H. Wang, C.M. Chang, and Y.L. Liu Benzoxazine-functionalized multi-walled carbon nanotubes for preparation of electrically-conductive polybenzoxazines Polymer 53 2012 106 112
38. M. Chapartegui, J. Barcena, X. Irastorza, C. Elizetxea, M. Fernandez, and A. Santamaria Analysis of the conditions to manufacture a MWCNT buckypaper/benzoxazine nanocomposite Compos Sci Technol 72 2012 489 497
39. M. Maleemullah, S.U. Khan, and J.K. Kim Effect of surfactant treatment on thermal stability and mechanical properties of CNT/polybenzoxazine nanocomposites Compos Sci Technol 72 2012 1968 1976
40. K.K. Ho, M.C. Hsiao, T.Y. Chou, C.C. Ma, X.F. Xie, and J.C. Chiang et al. Preparation and characterization of covalently functionalized graphene using vinylterminated benzoxazine monomer and associated nanocomposites with low coefficient of thermal expansion Polym Intern 62 2013 966 973
41. C.F. Wang, H.Y. Chen, S.W. Kuo, Y.S. Lai, and P.F. Yang Rapid, low temperature microwave synthesis of durable superhydrophobic carbon nanotube/polybenzoxazine nanocomposites RSC Adv 3 2013 9764 9769
42. M. Zeng, J. Wang, R.R. Li, J.X. Liu, W. Chen, and Q.Y. Xu et al. The curing behavior and thermal property of graphene oxide/benzoxazine nanocomposites Polymer 54 2013 3107 3116
43. 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 A Polym Chem 32 1994 1121 1129
44. J. Dunkers, and H. Ishida Reaction of benzoxazine-based phenolic resins with strong and weak carboxylic acids and phenols as catalysts J Polym Sci Part A Polym Chem 37 1999 1913 1921
45. A.W. Kawaguchi, A. Sudo, and T. Endo Polymerization-depolymerization system based on reversible addition-dissociation reaction of 1,3-benzoxazine with thiol ACS Macro Lett 2 2013 1 4
46. W.H. Hu, K.W. Huang, and S.W. Kuo Heterocucleobase-functionalized benzoxazine: synthesis, thermal properties, and self-assembled structure formed through multiple hydrogen bonding interactions Polym Chem 3 2012 1546 1554
47. F.W. Holly, and C.A. Cope Condensation products of aldehydes and ketones with o-aminobenzyl alcohol and o-hydrogy benzylamine J Am Chem Soc 66 1944 1875 1877
48. K. Chiou, and H. Ishida Incorporation of natural renewable components and waste byproducts to benzoxazine based high performance materials Curr Org Chem 17 2013 913 925
49. E. Calo, A. Maffezzoli, G. Mele, F. Martina, S.E. Mazzetto, and A. Tarzia et al. Synthesis of a novel cardanol-based benzoxazine monomer and environmentally sustainable production of polymers and bio-composites Green Chem 9 2007 754 759
50. S. Li, S. Yan, J. Yu, and B. Yu Synthesis and characterization of new benzoxazine-based phenolic resins from renewable resources and the properties of their polymers J Appl Polym Sci 5 2011 2843 2848
51. B. Lochab, I.K. Varma, and J. Bijwe Thermal behavior of cardanol-based benzoxazines Monom Polym 102 2010 769 774
52. K. Chiou, E. Hollanger, T. Agag, and H. Ishida Highly improved thermal properties of hydroxyl-containing polymers via modification by benzoxazine groups Macromol Chem Phys 214 2013 1629 1635
53. J.P. Raoa, and K.E. Geckelera Polymer nanoparticles: preparation techniques and size-control parameters Prog Polym Sci 36 2011 887 913
54. T. Takeichi, T. Kano, and T. Agag Synthesis and thermal cure of high molecular weight polybenzoxazine precursors and the properties of the thermosets Polymer 46 2005 12172 12180
55. H. Ishida, and D.J. Allen Mechanical characterization of copolymers based on benzoxazine and epoxy Polymer 37 1996 4487 4495
56. H. Ishida, and S. Ohba Thermal analysis and mechanical characterization of maleimide-functionalized benzoxazines/epoxy copolymers J Appl Polym Sci 101 2006 1670 1677
57. H.P.S. Abdul Khalil, M. Siti Alwani, and A.K. Mohd Omar Chemical composition, anatomy, lignin distribution, and cell wall structure of Malaysian plant waste fibers BioResources 1 2006 220 232
58. R.M. Rowell, J.S. Han, and J.S. Rowel Characterization and factors effecting fiber properties; natural polymers and agrofibers based composites Brazil 2000
59. E.M. Nour-Eddine, Q.L. Yuan, and F.R. Huang Investigation of curing and thermal behavior of benzoxazine and lignin mixtures J Appl Polym Sci 125 2012 1773 1781
60. H.M. Emranul Haque, Z. Islam, T. Kawauchi, and T. Takeichi Preparation and properties of polybenzoxazine/lignin alloy Appl Mech Mater 217-219 2012 571 577
61. M.B. Hocking Vanillin: synthetic flavoring from spent sulfite liquor J Chem Educ 74 1997 1055
62. H. Priefert, J. Rabenhorst, and A. Steinbuchel Biotechnical production of vanillin Appl Microbiol Biotechnol 56 2001 296 314
63. C. Fagues, A. Mathias, and A. Rodrigues Kinetics of vanillin production from Kraft lignin oxidation Ind Eng Chem Res 35 1996 28 36
64. E.A. Borges da Silva, M. Zabkova, J.D. Araujo, C.A. Cateto, M.F. Barreiro, and M.N. Belgacem et al. An integrated process to produce vanillin and lignin-based polyurethanes from Kraft lignin Chem Eng Res Des 87 2009 1276 1292
65. C. Sawaryn, K. Landfester, and A. Taden Benzoxazine miniemulsions stabilized with polymerizable nonionic benzoxazine surfactants Macromolecules 43 2010 8933 8941
66. C. Sawaryn, K. Landfester, and A. Taden Benzoxazine miniemulsions stabilized with multifunctional main-chain benzoxazine protective colloids Macromolecules 44 2011 5650 5658
67. N. Anton, J. Benoit, and P. Saulnier Design and production of nanoparticles formulated from nanoemulsion templates - a review J Control Release 128 2008 185 199
68. Q.C. Ran, Q. Tian, C. Li, and Y. Gu Investigation of processing, thermal, and mechanical properties of a new composite matrix-benzoxazine containing aldehyde group Polym Adv Technol 21 2010 170 176
69. Q.C. Ran, and Y. Gu Concerted reactions of aldehyde groups during polymerization of an aldehyde-functional benzoxazine J Polym Sci Part A Polym Chem 49 2011 1671 1677
70. 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
71. S. Chirachanchai, A. Laobuthee, and S. Phongtamrug Self termination of ring opening reaction of p-substituted phenol-based benzoxazines: an obstructive effect via intramolecular hydrogen bond J Heterocycl Chem 46 2009 714 721
72. A. Chernykh, J.P. Liu, and H. Ishida Synthesis and properties of a new crosslinkable polymer containing benzoxazine moiety in the main chain Polymer 47 2006 7664 7669
73. P.B. Pansuriya, P. Dhandhukia, V. Thakkar, and M.N. Patel Synthesis, spectroscopic and biological aspects of iron(II) complexes J Enzym Inhib Med Chem 22 2007 477 487
74. C.M. Ma, C. Lee, and H. Wu Mechanical properties, thermal stability, and flame retardance of pultruded fiber-reinforced poly(ethylene oxide)-toughened novlak-type phenolic resin J Appl Polym Sci 69 1998 1129 1136