Abstract
The development and progress of liquid crystalline epoxy resin technology and its applications are reviewed. The liquid crystalline epoxy resin exhibits superior chemical, mechanical, electrical, thermal properties than the conventional epoxy resin due to the presence of highly ordered liquid crystalline domain. That also results in extremely low permeation and toxicity behaviors. By incorporating nanofiller into the liquid crystalline epoxy resin to make into nanocomposite, the performance of the material is further improved which is suitable for wide range of applications in light weight structure, electrical insulation, electronic encapsulation, medical device and so on.
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References
Amendola E, Carfagna C, Giamberini M, Pisaniello G (1995) Curing reactions of a liquid-crystalline epoxy-resin based on the diglycidyl ether of 4,4′-dihydroxy-alpha-methylstilben. Macromol Chem Phys 196:1577–1591
Amendola E, Carfagna C, Giamberini M, Komitov L (1996) Anisotropic liquid crystalline epoxy thermoset. Liq Cryst 21:317–325
Balamurugan R, Kannan P (2009) Synthesis and properties of a liquid crystalline thermoset epoxy resin containing 1,3,4-oxadiazole groups. High Perform Polym 21:251–264
Balamurugan R, Kannan P (2010) 1,3,4-Oxadiazole epoxy resin-based liquid crystalline thermosets and their cure kinetics. J Mater Sci 45:1321–1327
Barclay GG, Ober CK, Papathomas KI, Wang DW (1992) Liquid-crystalline epoxy thermosets based on dihydroxymethylstilbene—synthesis and characterization. J Polym Sci Polym Chem 30:1831–1843
Cai ZQ, Sun JZ, Zhou QY, Xu JL (2007) Synthesis and characterization of a novel liquid-crystalline epoxy resin combining biphenyl and aromatic ester-type mesogenic units. J Polym Sci Polym Chem 45:727–735
Carfagna C, Amendola E, Giamberini M (1994a) Liquid-crystalline epoxy-resins—curing of blends of mesogenic and nonmesogenic epoxy monomers. J Mater Sci Lett 13:126–128
Carfagna C, Amendola E, Giamberini M (1994b) Liquid-crystalline epoxy-resins containing binaphthyl group as rigid block with enhanced thermal-stability. Macromol Chem Phys 195:2307–2315
Carfagna C, Amendola E, Giamberini M (1994c) Rigid-rod networks—liquid-crystalline epoxy-resins. Compos Struct 27:37–43
Carfagna C, Amendola E, Giamberini M, Filippov AG (1994d) Liquid-crystalline epoxy-resins—a glycidyl-terminated benzaldehyde azine cured in the nematic phase. Macromol Chem Phys 195:279–287
Carfagna C, Acierno D, Di Palma V, Amendola E, Giamberini M (2000a) Composites based on carbon fibers and liquid crystalline epoxy resins, 1—Monomer synthesis and matrix curing. Macromol Chem Phys 201:2631–2638
Carfagna C, Meo G, Nicolais L, Giamberini M, Priola A, Malucelli G (2000b) Composites based on carbon fibers and liquid crystalline epoxy resins, 2—dynamic-mechanical analysis and fracture toughness behavior. Macromol Chem Phys 201:2639–2645
Castell P, Galia M, Serra A (2001) Synthesis of new epoxy liquid-crystalline monomers with azo groups in the central mesogenic core. Crosslinking with amines. Macromol Chem Phys 202:1649–1657
Castell P, Serra A, Galia M (2003a) New liquid-crystal line thermosets from liquid-crystalline bisazomethynic epoxy resins with naphthylene disruptors in the central core. J Polym Sci Polym Chem 41:1536–1544
Castell P, Serra A, Galia M, Giamberini M, Carfagna C (2003b) Anisotropic thermosets from liquid-crystalline azomethynic epoxy resins and primary aromatic diamines. J Polym Sci Polym Chem 41:1–12
Castell P, Serra A, Galia M (2004) Liquid-crystalline thermosets from liquid-crystalline epoxy resins containing bisazomethinebiphenylene the central core: copolymerization with a nonmesomorphic epoxy resin. J Polym Sci Polym Chem 42:3631–3643
Chen S, Hsu SH, Wu MC, Su WF (2011) Kinetics studies on the accelerated curing of liquid crystalline epoxy resin/multiwalled carbon nanotube nanocomposites. J Polym Sci Polym Phys 49:301–309
Chiang CL, Ma CCM (2002) Synthesis, characterization and thermal properties of novel epoxy containing silicon and phosphorus nanocomposites by sol-gel method. Eur Polym J 38:2219–2224
Choi EJ, Ahn HK, Lee JK, Jin JI (2000) Liquid crystalline twin epoxy monomers based on azomethine mesogen: synthesis and curing with aromatic diamines. Polymer 41:7617–7625
Douglas EP (2002) Liquid crystalline thermosets. Encyclopedia of polymer science and technology, vol 3. Wiley, New York. doi:10.1002/0471440264
Duann YF, Liu TM, Cheng KC, Su WF (2004) Thermal stability of some naphthalene- and phenyl-based epoxy resins. Polym Degrad Stabil 84:305–310
Earls JD, Hefner RE, Puckett PM (1993) Mesogenic epoxy compounds. U.S. Patent 5,270,405
Gao Z, Yu Y, Xu Y, Li S (2007) Synthesis and characterization of a liquid crystalline epoxy containing azomethine mesogen for modification of epoxy resin. J Appl Polym Sci 105:1861–1868
Giamberini M, Amendola E, Carfagna C (1995) Curing of a rigid-rod epoxy resin with an aliphatic diacid—an example of a lightly cross-linked liquid-crystalline thermoset. Macromol Rapid Commun 16:97–105
Giamberini M, Amendola E, Carfagna C (1997) Lightly crosslinked liquid crystalline epoxy resins: the effect of rigid-rod length and applied stress on the state of order of the cured thermoset. Macromol Chem Phys 198:3185–3196
Grebowicz JS (1996) On the formation of liquid crystalline texture in epoxy resins. Macromol Symp 104:191–221
Harada M, Ochi M, Tobita M, Kimura T, Ishigaki T, Shimoyama N, Aoki H (2003) Thermal-conductivity properties of liquid-crystalline epoxy resin cured under a magnetic field. J Polym Sci Polym Phys 41:1739–1743
Harada M, Ochi M, Tobita M, Kimura T, Ishigaki T, Shimoyama N, Aoki H (2004) Thermomechanical properties of liquid-crystalline epoxy networks arranged by a magnetic field. J Polym Sci Polym Phys 42:758–765
Harada M, Watanabe Y, Tanaka Y, Ochi M (2006) Thermal properties and fracture toughness of a liquid-crystalline epoxy resin cured with an aromatic diamine crosslinker having a mesogenic group. J Polym Sci Polym Phys 44:2486–2494
Harada M, Sumitomo K, Nishimoto Y, Ochi M (2009) Relationship between fracture toughness and domain size of liquid-crystalline epoxy resins having polydomain structure. J Polym Sci Polym Phys 47:156–165
Harada M, Ando J, Hattori S, Sakurai S, Sakamoto N, Yamasaki T, Masunaga H, Ochi M (2013) In-situ analysis of the structural formation process of liquid-crystalline epoxy thermosets by simultaneous SAXS/WAXS measurements using synchrotron radiation. Polym J 45:43–49
Hirano Y, Akiba M, Yokota A, Nakamura H, Naitoh S (1999) Epoxy resin, resin composition, and resin-encapsulated semiconductor device. U.S. Patent 5,939,473
Hsu SH, Chen RS, Chang YL, Chen MH, Cheng KC, Su WF (2012a) Biphenyl liquid crystalline epoxy resin as a low-shrinkage resin-based dental restorative nanocomposite. Acta Biomater 8:4151–4161
Hsu SH, Wu MC, Chen S, Chuang CM, Lin SH, Su WF (2012b) Synthesis, morphology and physical properties of multi-walled carbon nanotube/biphenyl liquid crystalline epoxy composites. Carbon 50:896–905
Huo L, Gao J, Du Y, Chai Z (2008) Synthesis and characterization of the two novel liquid crystalline epoxy resins based on bisphenol-S mesogen. J Appl Polym Sci 110:3671–3677
Jahromi S, Lub J, Mol GN (1994) Synthesis and photoinitiated polymerization of liquid-crystalline diepoxides. Polymer 35:622–629
Le Hoang S, Shin S, Lim D-G, Nguyen Ngoc T, Bui Thanh S, Bae J-Y (2013) A novel wholly aromatic liquid crystalline epoxy monomer based on 2,7-naphthalene mesogen: Synthesis and curing with aromatic diamine. Macromol Res 21:1105–1109
Lee JY, Jang JS (1998) Effect of substituents on the curing of liquid crystalline epoxy resin. J Polym Sci Polym Chem 36:911–917
Lee JY, Jang JS (1999) Synthesis and curing of liquid crystalline epoxy resin based on naphthalene mesogen. J Polym Sci Polym Chem 37:419–425
Lee JY, Jang JS (2006) The effect of mesogenic length on the curing behavior and properties of liquid crystalline epoxy resins. Polymer 47:3036–3042
Lee H, Neville K (1967) Handbook of epoxy resins. McGraw-Hill, New York
Lee JY, Jang JS, Hwang SS, Hong SM, Kim KU (1998) Synthesis and curing of liquid crystalline epoxy resins based on 4,4′-biphenol. Polymer 39:6121–6126
Lee JY, Jang JS, Hong SM, Hwang SS, Kim KU (1999) Relationship between the structure of the bridging group and curing of liquid crystalline epoxy resins. Polymer 40:3197–3202
Li YZ, Kessler MR (2013) Liquid crystalline epoxy resin based on biphenyl mesogen: effect of magnetic field orientation during cure. Polymer 54:5741–5746
Li YZ, Kessler MR (2014) Creep-resistant behavior of self-reinforcing liquid crystalline epoxy resins. Polymer 55:2021–2027
Li YZ, Badrinarayanan P, Kessler MR (2013) Liquid crystalline epoxy resin based on biphenyl mesogen: thermal characterization. Polymer 54:3017–3025
Lin QH, Yee AF, Earls JD, Hefner RE, Sue HJ (1994) Phase-transformations of a liquid crystalline epoxy during curing. Polymer 35:2679–2682
Lin QH, Yee AF, Sue HJ, Earls JD, Hefner RE (1997) Evolution of structure and properties of a liquid crystalline epoxy during curing. J Polym Sci Polym Phys 35:2363–2378
Liu JP, Wang CC, Campbell GA, Earls JD, Priester RD (1997) Effects of liquid crystalline structure formation on the curing kinetics of an epoxy resin. J Polym Sci Polym Chem 35:1105–1124
Liu JP, Wang CC, Campbell GA, Earls JD, Priester RD (1998) The use of tetraalkylphosphonium-tetrafluoroborate-tetrafluoroboric acid in the curing of a liquid crystalline epoxy resin. J Polym Sci Polym Chem 36:1457–1471
Liu GD, Zhou B, Zhao DM, Li Q, Gao JG (2008) Novel triaromatic ester mesogenic liquid crystalline epoxy resin containing both methyl substituent and ethoxy flexible spacer: synthesis and curing. Macromol Chem Phys 209:1160–1169
Liu YL, Cai ZQ, Wang WC, Wen XF, Pi PH, Zheng DF, Cheng J, Yang ZR (2011a) Mechanical properties and morphology studies of thermosets from a liquid-crystalline epoxy resin with biphenol and aromatic ester groups. Macromol Mater Eng 296:83–91
Liu YL, Cai ZQ, Wen XF, Pi PH, Zheng DF, Cheng J, Yang ZR (2011b) Thermal properties and cure kinetics of a liquid crystalline epoxy resin with biphenyl-aromatic ester mesogen. Thermochim Acta 513:88–93
Mallon JJ, Adams PM (1993) Synthesis and characterization of novel epoxy monomers and liquid crystal thermosets. J Polym Sci Polym Chem 31:2249–2260
Mija A, Cascaval CN (2009) Liquid crystalline epoxy thermoset with azomethine mesogen. Polimery 54:786–789
Mittal V (2010) Optimization of polymer nanocomposite properties. Wiley-VCH, Weinheim
Mittal V (2013) Thermoset nanocomposites. Wiley-VCH, Weinheim
Mormann W, Broche M, Schwarz P (1997) Mesogenic azomethine based diepoxides—monomers for the synthesis of “liquid crystal” thermoset networks. Macromol Chem Phys 198:3615–3626
Mossety-Leszczak B, Włodarska M (2011) Liquid crystallinity in polymers—liquid crystalline epoxy resins. In: Iwan A, Schab-Balcerzak E (eds) Liquid crystalline organic compounds and polymers as materials of the XXI century: from synthesis to applications, Transworld Research Network, Kerala
Ochi M, Tsuyuno N, Sakaga K, Nakanishi Y, Murata Y (1995) Effect of network structure on thermal and mechanical-properties of biphenyl-type epoxy-resins cured with phenols. J Appl Polym Sci 56:1161–1167
Ochi M, Shimizu Y, Nakanishi Y, Murata Y (1997) Effect of the network structure on thermal and mechanical properties of mesogenic epoxy resin cured with aromatic amine. J Polym Sci Polym Phys 35:397–405
Ochi M, Hori D, Watanabe Y, Takashima H, Harada M (2004) Bonding properties of epoxy resins containing two mesogenic groups. J Appl Polym Sci 92:3721–3729
Ortiz C, Kim R, Rodighiero E, Ober CK, Kramer EJ (1998) Deformation of a polydomain, liquid crystalline epoxy-based thermoset. Macromolecules 31:4074–4088
Ortiz C, Belenky L, Ober CK, Kramer EJ (2000) Microdeformation of a polydomain, smectic liquid crystalline thermoset. J Mater Sci 35:2079–2086
Punchaipetch P, Ambrogi V, Giamberini M, Brostow W, Carfagna C, D'Souza NA (2001) Epoxy plus liquid crystalline epoxy coreacted networks: I. Synthesis and curing kinetics. Polymer 42:2067–2075
Ribera D, Mantecon A, Serra A (2001) Synthesis and crosslinking of a series of dimeric liquid crystalline epoxy resins containing imine mesogens. Macromol Chem Phys 202:1658–1671
Ribera D, Mantecon A, Serra A (2002) Liquid-crystalline thermosets from mesogenic dimeric epoxy resins by tertiary amine catalysis. J Polym Sci Polym Chem 40:3916–3926
Robinson EJ, Douglas EP, Mecholsky JJ (2002) The effect of stoichiometry on the fracture toughness of a liquid crystalline epoxy. Polym Eng Sci 42:269–279
Schnurpfeil G, Harder A, Schroder H, Wohrle D, Hartwig A, Hennemann OD (2001) Synthesis and photoinitiated polymerization of nematic liquid-crystalline diepoxides. Macromol Chem Phys 202:180–187
Shiota A, Ober CK (1996) Synthesis and curing of novel LC twin epoxy monomers for liquid crystal thermosets. J Polym Sci Polym Chem 34:1291–1303
Shiota A, Ober CK (1997) Analysis of smectic structure formation in liquid crystalline thermosets. Polymer 38:5857–5867
Smith JDB, Schoch J, K. F., A. SWF (1999) Electrical insulation using liquid crystal thermoset epoxy resins. U.S. Patent 5,904,984
Su WFA (1993) Thermoplastic and thermoset main-chain liquid-crystal polymers prepared from biphenyl mesogen. J Polym Sci Polym Chem 31:3251–3256
Su WFA, Chuang CM (2002) Effects of chemical structure changes on curing reactions and thermal properties of cyanate ester-cured rigid-rod epoxy resins. J Appl Polym Sci 85:2419–2422
Su WFA, Schoch KF, Smith JDB (1998) Comparison of cure conditions for rigid rod epoxy and bisphenol a epoxy using thermomechanical analysis. J Appl Polym Sci 70:2163–2167
Su WFA, Chen KC, Tseng SY (2000) Effects of chemical structure changes on thermal, mechanical, and crystalline properties of rigid rod epoxy resins. J Appl Polym Sci 78:446–451
Su WF, Fu YC, Pan WP (2002a) Thermal properties of high refractive index epoxy resin system. Thermochim Acta 392:385–389
Su WF, Huang HW, Pan WP (2002b) Thermal properties of rigid rod epoxies cured with diaminodiphenylsulfone and dicyandiamide. Thermochim Acta 392:391–394
Su WF, Lee YC, Pan WP (2002c) Thermal properties of phthalic anhydride- and phenolic resin-cured rigid rod epoxy resins. Thermochim Acta 392:395–398
Su WF, Hsu SH, Tai YY, Chen MH (2012) Liquid crystalline epoxy nanocomposite material and application thereof U.S. Patent 8,309,632
Sue HJ, Earls JD, Hefner RE (1997) Fracture behaviour of liquid crystal epoxy resin systems based on the diglycidyl ether of 4,4′-dihydroxy-alpha-methylstilbene and sulphanilamide. 1. Effects of curing variations. J Mater Sci 32:4031–4037
Szczepaniak B, Frisch KC, Penczek P, Rejdych J, Winiarska A (1997) Curing of liquid crystalline epoxy resins with a biguanide. J Polym Sci Polym Chem 35:2739–2745
Tai YY, Hsu SH, Chen RS, Su WF, Chen MH (2014) Liquid crystalline epoxy nanocomposite material for dental application. J Formos Med Assoc 114:46–51
Tanaka S, Takezawa Y, Takahashi H (2007) Epoxy compound and cured epoxy resin product. U.S. Patent 7,279,574
Twardowski TE (2007) Introduction to nanocomposite materials: properties, processing. Characterization. DEStech Publications, Inc., Lancaster
Vengatesan MR, Devaraju S, Alagar M (2011) Studies on thermal, mechanical and morphological properties of organoclay filled azomethine modified epoxy nanocomposites. High Perform Polym 23:3–10
Vittoria V, Russo R, Decandia F, Magagnini PL, Bresci B (1991) Transport-properties of a side-chain liquid-crystalline polymer—poly(4-acryloyloxy biphenyl). J Polym Sci Polym Phys 29:1163–1168
Vyazovkin S, Mititelu A, Sbirrazzuoli N (2003) Kinetics of epoxy-amine curing accompanied by the formation of liquid crystalline structure. Macromol Rapid Commun 24:1060–1065
Wang HM, Zhang YC, Zhu LR, Zhang BL, Zhang YY (2011) Synthesis and curing behavior of a novel liquid crystalline epoxy resin. J Therm Anal Calorim 103:1031–1037
Weinkauf DH, Paul DR (1992) Gas-transport properties of thermotropic liquid-crystalline copolyesters. 1. The effects of orientation and annealing. J Polym Sci Polym Phys 30:817–835
Wlodarska M, Bak G, Mossety-Leszczak B, Galina H (2009) Influence of liquid crystalline ordering on the properties of selected cured nematic epoxy materials. J Mater Process Tech 209:1662–1671
Xiao Y, Cao L, Feng JH, Yuan LJ (2012) Synthesis and curing of liquid crystalline epoxy resin based on asymmetric mesogen. J Appl Polym Sci 126:527–535
Yamamoto H, Fujita A, Harada M, Ochi M (2014) Synthesis and characterization of novel liquid crystalline epoxy resin with low melting point. Mol Cryst Liq Cryst 588:41–50
Zhou DW, Lu MG, Liang LY, Shen TF, Xiao WP (2012) Curing behavior of Azo-containing twin liquid crystalline epoxy resins with anhydride. Polym Eng Sci 52:1375–1382
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The authors would like to thank Miss Shiow-Wei Wang, Miss Yin-Hsi Lin and Mr. Chun-Fu Lu for their help in the preparation of this manuscript.
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Hsu, SH., Chen, MH., Su, WF. (2015). Liquid Crystalline Epoxy Resin Based Nanocomposite. In: Thakur, V., Kessler, M. (eds) Liquid Crystalline Polymers. Springer, Cham. https://doi.org/10.1007/978-3-319-20270-9_19
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