Synthesis, curing kinetics and thermal properties of novel difunctional chiral and achiral benzoxazines with double chiral centers

Journal of Thermal Analysis and Calorimetry

Volumn 114, Issue 3, 2013, Pages 1255-1264

  Wang, Jun ^a   Wang, Hui ^a   Liu, Jun Ting ^a   Liu, Wen Bin ^a   Shen, Xian De ^a  

^a HARBIN ENGINEERING UNIVERSITY   (China)

Author keywords

Achiral benzoxazine; Chiral benzoxazine; Curing kinetics; Polymerization behavior; Thermal properties

Indexed keywords

BENZOXAZINE; BENZOXAZINE MONOMERS; CURING KINETICS; DIFFERENTIAL SCANNING CALORIMETERS; FOURIER TRANSFORM INFRA REDS; INTERMOLECULAR HYDROGEN BONDS; ISO-CONVERSIONAL METHOD; POLYMERIZATION BEHAVIOR;

ACETAL RESINS; DIFFERENTIAL SCANNING CALORIMETRY; HYDROGEN BONDS; ISOMERS; KINETICS; MONOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMER BLENDS; POLYMERS; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL); THERMODYNAMIC PROPERTIES; THERMOGRAVIMETRIC ANALYSIS;

CURING;

EID: 84890119694     PISSN: 13886150     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10973-013-3081-8     Document Type: Article

References (60)

1. Ishida H, Agag T. Handbook of benzoxazine resins. Oxford: Elsevier; 2011.
2. Yagci Y, Kiskan B, Ghosh NN. Recent advancement on polybenzoxazine - A newly developed high performance thermoset. J Polym Sci, Part A: Polym Chem. 2009;47:5565-76.
3. Ghosh NN, Kiskan B, Yagci Y. Polybenzoxazines - New high performance thermosetting resins synthesis and properties. Prog Polym Sci. 2007;32:1344-91.
4. 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, Part A: Polym Chem. 2008;46:414-20.
5. Temel G, Esen DN, Arsu N. One-component benzoxazine type photoinitiator for free radical polymerization. Polym Eng Sci. 2012;52:133-8.
6. Ning X, Ishida H. Phenolic materials via ring-opeaning polymerization: synthesis and characterization of bisphenol-A based benzoxazines and their polymers. J Polym Sci, Part A: Polym Chem. 1994;32:1121-9.
7. Velez-Herrera P, Doyama K, Abe H, Ishida H. Synthesis and characterization of highly fluorinated polymer with the benzoxazine moiety in the main chain. Macromolecules. 2008;41:9704-14.
8. Lin CH, Cai SX, Leu TS, Hwang TY, Lee HH. Synthesis and properties of flame-retartant benzoxazines by three approaches. J Polym Sci Part A: Polym Chem. 2006;44:3454-68.
9. Agag T, Jin L, Ishida H. A new synthetic approach for difficult benzoxazines: preparation and polymerization of 4,4′-diaminodiphenyl sulfone-based benzoxazine monomer. Polymer. 2009;50:5940-4.
10. Wang YX, Ishida H. Synthesis and properties of new thermoplastic polymers from substituted 3,4-dihydro-2H-1,3-benzoxazines. Macromolecules. 2000;33:2839-47.
11. Li SF, Yan SL, Yu JY, Yu B. Synthesis and characterization of new benzoxazine-based phenolic resins from renewable resources and the properties of their polymers. J Appl Polym Sci. 2011;122:2843-8.
12. Shen S, Ishida H. Development and characterization of high-performance polybenzoxazine composites. Polym Compos. 1996;17:710-9.
13. Agag T, Akelah A, Rehab A, Mostafa S. Flexible polybenzoxazine thermosets containing pendent aliphatic chains. Polym Int. 2012;61:124-8.
14. Lochab B, Varma IK, Bijwe J. Blends of benzoxazine monomers effect of structure and composition on polymer properties. J Therm Anal Calorim. 2013;111:1357-64.
15. Takeichi T, Guo Y, Agag T. Synthesis and characterization of poly(urethane-benzoxazine) films as novel type of polyurethane/phenolic resin composites. J Polym Sci, Part A: Polym Chem. 2008;38:4165-76.
16. Agag T, Takeichi T. Polybenzoxazine-montmorillonite hybrid nanocomposites: synthesis and characterization. Polymer. 2000;41:7083-90.
17. Kumar SKS, Nair RCP, Sadhana R, Ninan KN. Benzoxazine-bismaleimide blends: curing and thermal properties. Eur Polym J. 2007;43:5084-96.
18. Takeichi T, Saito Y, Agag T, Muto H, Kawauchi T. Performance enhancement of polybenzoxazine by hybridization with polysiloxane. Polymer. 2008;49:1173-9.
19. Kumar SKS, Nair RCP, Ninan KN. Investigation on the cure chemistry and polymer properties of benzoxazine-cyanate ester blends. Eur Polym J. 2009;45:494-502.
20. Li XD, Gu Y. The co-curing progress of a benzoxazine-cyanate system and the thermal properties of the copolymers. Polym Chem. 2011;2:2778-81.
21. Ishida H, Ohba S. Synthesis and characterization of maleimide and norbornene functionalized benzoxazines. Polymer. 2005;46:5588-95.
22. Lochab B, Varma IK, Bijwe J. Thermal behaviour of cardanol-based benzoxazine: monomers and polymers. J Therm Anal Calorim. 2010;102:769-74.
23. Wang J, Wu MQ, Liu WB, Yang SW, Bai JW, Ding QQ, Li Y. Synthesis, curing behavior and thermal properties of fluorene containing benzoxazines. Eur Polym J. 2010;46:1024-31.
24. Liu YF, Zhang HL, Wang M, Liao CY, Zhang J. Thermal degradation behavior and mechanism of polybenzoxazine based on bisphenol-S and methylamine. J Therm Anal Calorim. 2012. doi: 10.1007/s10973-012-2678-7.
25. Liu YF, Li ZH, Zhang J, Zhang HL, Fan HY, Run MT. Polymerization behavior and thermal properties of benzoxazine based on 4,4′-diaminodiphenyl ether. J Therm Anal Calorim. 2013;111:1523-30.
26. Yang P, Gu Y. A novel benzimidazole moiety-containing benzoxazine: synthesis, polymerization and thermal properties. J Polym Sci A: Polym Chem. 2012;50:1261-71.
27. Lochab B, Varma IK, Bijwe J. Cardanol based bisbenzoxazines: effect of structure on thermal behaviour. J Therm Anal Calorim. 2012;107:661-8.
28. Ishida H, Low HY. A study on the volumetric expansion of benzoxazine-based phenolic resin. Macromolecules. 1997;30:1099-106.
29. Spontón M, Lligadas G, Ronda JC, Galià M, Cádiz V. Development of a DOPD-containing benzoxazine and its high-performance flame retardant copolybenzoxazines. Polym Degrad Stab. 2009;94:1693-9.
30. He XC, Eliet EL. Highly enantioselective syntheses of α-hydroxyacids using N-benzyl-4,4,7α-trimethyl-trans-octahydro-1,3- benzoxazine as a chiral adjuvant. Tetrahedron. 1987;43:4979-87.
31. Pedrosa R, Andrés C, Mendiguchía P, Nieto J. Diastereoselective synthesis of enantiopure morpholines by electrophilic selenium-induced 6-exo cyclizations on chiral 3-allyl-2-hydroxymethylperhydro-1, 3-benzoxazine derivatives. J Org Chem. 2006;71:8854-63.
32. Thienthong N, Perlmutter P. A new class of nitrogen based chiral ligands: 2H-1,3-benzoxazines Ligand synthesis, X-ray structural studies and asymmetric catalysis. J Organomet Chem. 2006;690:2027-34.
33. Bernardinelli GH, Kündiq EP, Meier P, Pfaltz A, Radkowski K, Zimmermann N, Neuburger-Zehnder M. Chiral bidentate (phosphinophenyl) benzoxazine ligands in asymmetric catalysis. Helv Chim Acta. 2001;84:3233-46.
34. Ejfler J, Krauzy-Dziedzic K, Szafert S, Lis T, Sobota P. Novel chiral and achiral benzoxazine monomers and their thermal polymerization. Macromolecules. 2009;42:4008-15.
35. Wang J, Fang X, Wu MQ, He XY, Liu WB, Shen XD. Synthesis, curing kinetics and thermal properties of bisphenol-AP-based benzoxazines. Eur Polym J. 2011;47:2158-68.
36. Dunkers J, Ishida H. Vibrational assignments of N,N-bis(3,5-dimethyl-2- hydroxybenzyl) methyl-amine in the fingerprint region. Spectrochim Acta. 1995;51:855-67.
37. Larkin P. Infrared and Raman Spectroscopy: principles and spectral interpretation. San Diego: Elsevier; 2011.
38. Lin CH, Chang SL, Hsieh CW, Lee HH. Aromatic diamine-based benzoxazines and their high performance thermosets. Polymer. 2008;49:1220-9.
39. Kumar SKS, Nair RCP, Radhakrishnan TS, Ninan KN. Bis allyl benzoxazine: synthesis, polymerisation and polymer properties. Eur Polym J. 2007;43:2504-14.
40. Ishida H, Rodriguez Y. Curing kinetics of a new benzoxazine-based phenolic resin by differential scanning calorimetry. Polymer. 1995;36:3151-8.
41. Ishida H, Rodriguez Y. Catalyzing the curing reaction of a new benzoxazine-based phenolic resin. J Appl Polym Sci. 1995;58:1751-60.
42. Gârea SA, Iovu H, Nicolescu A, Deleanu C. Thermal polymerization of benzoxazine monomers followed by GPC, FTIR. DETA. Polym Test. 2007;26:162-71.
43. Ishida H, Sanders DP. Regioselectivity and network structure of difunctional alkyl-substituted aromatic amine-based polybenzoxazines. Macromolecules. 2000;33:8149-57.
44. Takeichi T, Guo Y, Rimdusit S. Performance improvement of polybenzoxazine by alloying with polyimide: effect of preparation method on the properties. Polymer. 2005;46:4909-16.
45. Kim HD, Ishida H. Model compounds study on the network structure of polybenzoxazines. Macromolecules. 2003;36:8320-9.
46. Lin CH, Chang SL, Shen TY, Shih YS, Lin HT, Wang CF. Flexible polybenzoxazines thermosets with high glass transition temperatures and low surface free energies. Polym Chem. 2012;3:935-45.
47. Kim HD, Ishida H. A study on hydrogen-bonded network structure of polybenzoxazines. J Phys Chem A. 2002;106:3271-80.
48. Andronescu C, Gârea SA, Deleanu C, Iovu H. Characterization and curing kinetics of new benzoxazine monomer based on aromatic diamines. Thermochimi Acta. 2012;530:42-51.
49. Lu YB, Li MM, Ke LL, Hu D, Xu WJ. Curing kinetics of fluorene containing benzoxazine investigated by nonisothermal differential scanning calorimetry. J Appl Polym Sci. 2011;121:2481-7.
50. Ke LL, Hu D, Lu YB, Feng S, Xie YY, Xu WJ. Copolymerization of maleimide-based benzoxazine with styrene and the curing kinetics of the resultant copolymer. Polym Degrad Stab. 2012;97:132-8.
51. Chow WS, Grishchuk S, Burkhart T, Karger-Kocsis J. Gelling and curing behaviors of benzoxazine/epoxy formulations containing 4,4′-thiodiphenol accelerator. Thermochimi Acta. 2012;543:172-7.
52. Zhang C, Binienda WK, Zeng L, Ye X, Chen S. Kinetic study of the novolac resin curing process using model fitting and model-free methods. Thermochim Acta. 2011;523(1-2):63-9.
53. Vyazovkin S. Computational aspects of kinetic analysis. Part C. The ICTAC kinetics project - the light at the end of the tunnel? Thermochim Acta. 2000;355(1-2):155-63.
54. Starink MJ. The determination of activation energy from linear heating rate experiments: a comparison of the accuracy of isoconversion methods. Thermochim Acta. 2003;404(1-2):163-76.
55. Friedman HL. Kinetics of thermal degradation of char-forming plastics from thermogravimetry. Application to a phenolic plastic. J Polym Sci Part C. 1964;6:183-95.
56. Pérez JM, Oliet M, Alonso MV, Rodríguez F. Curing kinetics of lignin-novolac resins studied by isoconversional methods. Thermochimi Acta. 2009;487:39-42.
57. Akahira T, Sunose T. Method of determining activation deterioration constant of electrical insulating materials. Res Rep Chiba Inst Technol. 1971;16:22-31.
58. Spontón M, Larrechi MS, Ronda JC, Galià M, Cádiz V. Synthesis and study of the thermal crossling of bis(m-aminophenyl) methylphosphine oxide based benzoxazine. J Polym Sci, Part A: Polym Chem. 2008;46:7162-72.
59. Ishida H, Allen DJ. Physical and mechanical characterization of near-zero shrinkage polybenzoxazines. J Polym Sci, Part B: Polym Phys. 1996;34:1019-30.
60. Low HY, Ishdia H. Mechanistic study on the thermal decomposition of polybenzoxazines: effects of aliphatic amines. J Polym Sci, Part B: Polym Phys. 1998;36:1935-46.